The way to obtain unsymmetrical 4,6-bis(aryloxy) pyrimidine intermediate connection

 

(57) Abstract:

The invention relates to an improved method for producing unsymmetrical 4,6-bis(aryloxy)pyrimidine of formula I, which are used in agriculture as pesticides, and to a new intermediate compound of formula II to obtain it. The method of obtaining the compounds of formula I, where the values of the radicals indicated in the claims, provided that at least one of R2and R6is not hydrogen and alloctype not the same, involves reacting 4,6-dehalogenation formula III, where X is C1, Br or I, with one or less than the molar equivalent of the first phenol of the formula IV and the first base in the presence of a first solvent to obtain 4-halo-6-(aryloxy)pyrimidine of the formula V, which interacts with approximately one molar equivalent WITH1-C4-trialkylamine, in the presence of a second solvent to obtain compounds of formula II, where Q denotes a group R9R10R11N+- and the interaction of the ammonium halide with at least one molar equivalent of the second phenol of formula VI and the second base in the presence of a third solvent. The method allows policitians, than in the known methods. 2 C. and 8 C.p. f-crystals.

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Symmetrical and unsymmetrical 4,6-bis(aryloxy)pyrimidines which are useful as pesticides, are described in WO 94/02470. Symmetric 4,6-bis(aryloxy)pyrimidines receive a one-step reaction of 4,6-dehalogenation with two molar equivalents of phenol. In contrast, unsymmetrical 4,6-bis(aryloxy)pyrimidines get much more difficult, because alloctype need to enter through a separate reactions.

In WO 94/02470 described that unsymmetrical 4,6-bis(aryloxy) pyrimidine is obtained by interaction of 4,6-developerkeys with one molar equivalent of the first phenol in the presence of a base and then the interaction of the compounds with a second phenol in the presence of a base. However, this method is not entirely satisfactory for the industrial production of unsymmetrical 4,6-bis(aryloxy)pyrimidine. When using 4,6-dichloropyrimidine is mixed substitution arroxyjoype, resulting, as shown in reaction scheme I (at the end of the description), symmetrical compounds that are difficult to separate from the target unsymmetrical product.

For decisions about. what, however, 4,6-giftability obtained from 4,6-dichloropyrimidine halogenoalkanes reaction, which requires the use of expensive reagents and consumption of large amounts of energy.

Therefore, the present invention is to provide a method of obtaining unsymmetrical 4,6-bis(aryloxy)pyrimidine, which would eliminate the disadvantages of the known methods.

Summary of the invention

The present invention relates to a method for unsymmetrical 4,6-bis(aryloxy)pyrimidine having the structural formula I

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where R and R8each independently represents hydrogen or halogen;

R1and R7each independently represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, alkoxyalkyl, haloalkoxy or alkoxycarbonyl;

R2and R6each independently represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl, haloalkyl, haloalkoxy, alkoxycarbonyl, Gloucestershire, haloalkaliphilic, haloalkaliphilic, nitro or cyano;

R3and R5each independently represents hydrogen, halogen, alkyl or alkoxy and

R2and R6is not hydrogen and that alloctype not the same; which involves reacting 4,6-dehalogenation, having structural formula II

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where R4such as the one above, and X is C1, Br or I, with one or less than the molar equivalent of the first phenol having the structural formula III

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where R, R1, R2and R3such as described above, and the first base in the presence of a first solvent to obtain 4-halo-6-(aryloxy)pyrimidine having the structural formula IV

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where R, R1, R2, R3, R4and X such as described above, the interaction of 4-halo-6-(aryloxy)pyrimidine with at least about one molar equivalent WITH1-C4-trialkylamine, in the presence of a second solvent to obtain compounds of ammonium halide having the structural formula V

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where R, R1, R2, R3, R4and X such as described above, Q+represents a

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R9, R10and R11each independently represents C1-C4-alkyl and taken together, R9and R10may form a 5 - or 6-membered ring, in which the group R is e n represents the integer 3, 4 or 5, provided that R11is1-C4-alkyl;

Z represents Oh, 5 or NR14;

R12and R13each independently represents hydrogen, C1-C4-alkyl or C1-C4-alkoxy, and when taken together R12and R13may form a 5 - or 6-membered saturated or unsaturated ring, optionally broken O, S or NR14and optionally substituted with one to three C1-C4-alkyl groups or WITH1-C4-alkoxygroup and

R14is1-C4-alkyl;

and the interaction of the compounds of the ammonium halide with at least about one molar equivalent of the second phenol having the structural formula VI

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where R5, R6, R7and R8such as described above, and the second base in the presence of a third solvent to obtain the desired compounds of formula I.

The advantage of this method is that the method according to the present invention provides asymmetric bis(aryloxy)pyrimidines with a higher yield than the known methods, eliminates the problem of mixed substitution associated with use in a known way 4,6-dichloropyrimidine, and the ASS="ptx2">

Detailed description of the invention

The method preferably includes the interaction described above 4,6-developerkeys formula II with one molar equivalent of the above-described first phenol of formula III and at least one molar equivalent of the first base in the presence of a first solvent preferably at a temperature in the range from approximately 0 to 100oWith obtaining 4-halo-6-(aryloxy)pyrimidine of formula IV described above, the interaction of the compounds of formula IV with at least about one molar equivalent of the above amine in the presence of the second solvent preferably at a temperature in the range from approximately 0 to 100oC obtaining the above-described compounds of the ammonium halide of the formula V and the interaction of the compounds of formula V with one molar equivalent of the second phenol of formula VI and at least about one molar equivalent of the second base in the presence of a third solvent preferably at a temperature in the range from approximately 0 to 100oWith obtaining the target unsymmetrical 4,6-bis(aryloxy)pyrimidine of formula I. Scheme of reactions shown in reaction scheme II (at the end of the description).

Unsymmetrical 4,6-bis(aryloxy) is as formula I. The compounds of formula I can also be distinguished by extracting the aqueous mixture with a suitable solvent. Suitable solvents for extraction include essentially not miscible with water solvents, such as diethyl ether, ethyl acetate, toluene, methylene chloride, and the like.

The ammonium halides are particularly important feature of the present invention. In the interaction of the ammonium halide with a second phenol mixed substitution by arroxyjoype does not occur. Unexpectedly the present invention has eliminated the disadvantage in mixed substitution arroxyjoype without using 4,6-giftability.

Amines that can be used in the method according to the present invention for obtaining ammonium halides, are bonds alkylamines, 5-6-membered saturated, and 5-14 membered unsaturated heterocyclic amines, optionally substituted one to three WITH1-C4-alkyl groups or WITH1-C4-alkoxygroup. Preferred amines are1-C4-trialkylamine, 5 - or 6-membered saturated heterocyclic amines and 5-14 membered unsaturated heterocyclic amines in which heterocycle.

The most preferred amines include trimethylamine, saturated heterocyclic amines, including pyridine, pikolines, pyrazine, pyridazine, triazine, quinoline, isoquinolines, imidazoles, benzothiazole and benzimidazole, optionally substituted with one to three WITH1-C4-alkyl groups or WITH1-C4-alkoxygroup, and unsaturated heterocyclic amines, such as pyrrolidine, piperidine, piperazines, morpholines, thiazolidine and thiomorpholine.

First and second base, suitable for use in the method according to the present invention include carbonates of alkali metals such as sodium carbonate and potassium carbonate, carbonates of alkaline earth metals such as calcium carbonate and magnesium carbonate, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, and preferred are carbonates of alkali metals.

Suitable for use first solvents include ethers, such as diatrofi ether, tetrahydrofuran and dioxane, amides of carboxylic acids, such as N,N-dimethylformamide and N,N-dimethylacetamide, halogenated the AK sulfoxide, ketones, such as acetone and N-organic, and mixtures thereof. Second solvents suitable for use in the method according to the present invention, include aromatic hydrocarbons such as toluene, xylene and benzene, halogenated aromatic hydrocarbons, such as chlorobenzene and dichlorobenzene, and mixtures thereof. Third solvents suitable for use in the proposed method, include amides of carboxylic acids, such as N,N-dimethylformamide and N,N-dimethylacetamide, sulfoxidov, such as dimethyl sulfoxide and mixtures thereof.

Preferred first solvents include amides of carboxylic acids and ketones. Preferred second solvents include aromatic hydrocarbons. And third preferred solvents include amides of carboxylic acids.

In the above formula I suitable alkyl group is a group with an unbranched or branched chain containing up to 8 carbon atoms, for example up to 6 carbon atoms. In accordance with a preferred variant of the invention the alkyl group contains up to 4 carbon atoms. The alkyl fragment that forms part of another group, for example alkyl halogenosilanes group or each alkyl alkoxyalkyl is laroda.

In the above formula, the halogen is fluorine, chlorine, bromine or iodine. Halogenated, halogenoalkane are, in particular, trifluoromethyl, pentafluoroethyl, triptoreline.

The method according to the present invention is particularly useful to obtain unsymmetrical 4,6-bis(aryloxy)pyrimidines of the formula I, where

R and R8the same and each represents hydrogen or fluorine;

R1and R7each independently represents hydrogen, halogen, cyano, nitro or1-C4-alkyl;

R2and R6each independently represents hydrogen, fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl,1-C4-haloalkoxy,2-C4-haloalkyl,1-C4-alkoxycarbonyl or nitro;

R3and R5each independently represents hydrogen, halogen or1-C4-alkyl and

R4represents hydrogen, C1-C4-haloalkyl,1-C4-alkylthio,1-C4-alkylsulfonyl or phenyl;

provided that at least one of the radicals R2and R6is not hydrogen and that alloctype not the same.

In particular, the method according to the present invention is used to receive establet hydrogen;

one of the radicals R1and R7represents hydrogen, chlorine or cyano and the other is fluorine and

R2and R8represent trifluoromethyl.

For a better understanding of the invention below presents examples that illustrate it more specifically. These examples should not limit the scope of the invention defined in the claims.

EXAMPLE 1

Getting 4[(4-chloro-,,,-Cryptor-m-tolyl)oxy]-6-[(,,,4-titrator-m-tolyl)oxy]pyrimidine - the method according to the present invention

a) Obtaining 4-chloro-6[(,,,4 titrator-m-tolyl)oxy]-pyrimidine

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To a mixture of 4,6-dichloropyrimidine (1000,0 g of 6.71 mol) and potassium carbonate (967,5 g, 7,00 mol) in N, N-dimethylformamide (10 l) was slowly added (,,,4 titrator-m-cresol (1208,9 g of 6.71 mol). The reaction mixture was stirred over night at room temperature, 2 hours at 45oC, 2 hours at 71oC and overnight at room temperature and poured into water (20 l). The resulting aqueous mixture was extracted with methylene chloride. The organic extracts were combined, washed successively with water, 5% sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo, resulting in the specified header is]-4-pyrimidyl} ameriglide

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To a solution of 4-chloro-6-[(,,,4-titrator-m-tolyl)oxy]-pyrimidine (2038,8 g, 6,97 mol) in toluene (17 l) was added condensed trimethylamine (1255, 21,24 mol). The reaction mixture was stirred over night at room temperature and was filtered. The obtained solid substance was washed successively with toluene and hexane and dried overnight in a vacuum oven at 60-65oWith, with a specified title product as a white solid (1962 g, yield 80%).

C) Obtaining 4-[(4-chloro-,,,-Cryptor-m-tolyl)oxy]-6-[(,,,4-titrator-m-tolyl)oxy] pyrimidine

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To a mixture of trimethyl 6-[(,,,4 titrator-m-tolyl)oxy]-4-pyrimidyl of ammoniaand (1962,0 g, 5,58 mol) and potassium carbonate (793,2 g, 5,74 mol) in N, N-dimethylformamide (8.5 l) was added,,,4 titrator-m-cresol (1118,9 g, 5,69 mol). The reaction mixture was stirred overnight at room temperature, cooled to 5oAnd slowly diluted with water (2,27 l). The resulting aqueous mixture was filtered to obtain a solid substance. The solid is washed successively with water, hexane and water, dried overnight in a vacuum oven at 40-45oWith and recrystallized from hexanol, receiving specified in title product as yellow terdam 55% when using as a starting reagent 4,6-dichloropyrimidine.

EXAMPLE 2

Poluchenie-[(4-chloro-,,,-Cryptor-m-tolyl)oxy]-6-[(,,,4-titrator-m-tolyl)oxy] pyrimidine - known method using 4,6-giftability

a) Obtaining 4,6-giftability

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A mixture of 4,6-dichloropyrimidine (223,5 g, 1.5 mol), potassium fluoride (279,6 g, 4.8 mol) and tetrabutylammonium (6.0 g, 0,0186 mol) in sulfolane (1 l) was heated at 180-190oWith over 3.5 hours and distilled to receive specified in the procurement of the product as a white liquid (115 g, yield 66%).

b) Receiving 4[(4-chloro-,,,-Cryptor-m-tolyl)oxy]-6-ftorpirimidinu

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To a solution of 4,6-giftability (44 g, 0,379 mol) and trifter-4-chloro-m-cresol (72.5 g, 0,369 mol) in methylene chloride (270 ml) was slowly added a solution of sodium hydroxide (14.8 g, and 0.37 mol) and Tetramethylammonium (0,928 g, 0,00847 mol) in water (140 ml). The reaction mixture was stirred at room temperature for 2 hours and separated phases. The aqueous phase was extracted with methylene chloride and the organic extract was combined with the organic phase. The resulting organic solution was washed for 1 H. sodium hydroxide solution, dried over anhydrous magnesium sulfate and concentrated in vacuo, resulting in a solid substance. Hard substance paracrystal is 6%).

C) Obtaining 4-[(4-chloro-,,-Cryptor-m-tolyl)oxy]-6-[(,,,4-titrator-m-tolyl)oxy]pyrimidine 6

To a mixture of 4-[(4-chloro-,,-Cryptor-m-tolyl)oxy]-6-fluoro-pyrimidine (97 g, 0.33 mol) and potassium carbonate (91,5 g, 0.66 mol) in N,N-dimethylformamide (200 ml) was added over 5 minutes a solution ,,,4 titrator-m-cresol (59,7 g, 0.33 mol) in N,N-dimethylformamide (150 ml). The reaction mixture was stirred at room temperature for 4.5 hours, treated with additional quantity ,,,4 titrator-m-cresol (6 g), was stirred at room temperature for one hour, treated with additional quantity ,,,4 titrator-m-cresol (2 g), was stirred overnight at room temperature, was treated with an additional quantity ,,,4 titrator-m-cresol (1 g), was stirred at room temperature for 1 hour and was poured into a mixture of ice water (1780). The resulting aqueous mixture was stirred for 2 hours and filtered to obtain a solid substance. The solid was dissolved in methylene chloride and the organic solution was washed sequentially 2 N. a solution of sodium hydroxide and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo, resulting in a white solid. White solid is 91%).

As you can see from the data in example 2, a known method using 4,6-giftability, using as starting reagent 4,6-dichloropyrimidine gives the target product with a yield of 40%.

EXAMPLE 3

Getting 4[(4-chloro-,,-Cryptor-m-tolyl)oxy] -6-[(,,,4-titrator-m-tolyl)oxy] pyrimidine - known method using 4,6-dichloropyrimidine

a) Obtaining 4-chloro-6[(,,,4 titrator-m-tolyl)oxy]-pyrimidine

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4-Chloro-6-[(,,,4-titrator-m-tolyl)oxy] pyrimidine was obtained with a yield of 99% according to the method described in example 1.

b) Obtaining 4-[(4-chloro-,,-Cryptor-m-tolyl)oxy]-6-[(,,,4-titrator-m-tolyl)oxy]pyrimidine

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A solution of 4-chloro-6[(,,,4 titrator-m-tolyl)oxy]pyrimidine (0.25 g, 0.6 mmol),,,, trifter-4-chloro-m-cresol (0.12 g, 0.6 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in N,N-dimethylformamide was heated to 60oWith c by stirring at this temperature for 24 hours, cooled and poured into water. The aqueous mixture was extracted with ether and the organic extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo, resulting in a solid (0.21 g). Solid, as it was found, contained above the target product and two SIMM is on the hard, but before the separation clearly that the yield of the target compound is only about 30%.

Thus, the advantage of the method according to the present invention is that it provides a significantly higher yield (55% instead of 40% and 30%) 4-[(4-chloro-,,-Cryptor-m-tolyl)oxy]-6[(,,,4 titrator-m-tolyl)-oxy]pyrimidine compared with known methods.

EXAMPLE 4

Getting 4-[(,,-Cryptor-4-nitro-m-tolyl)oxy]-6-[(,,-Cryptor-m-tolyl)oxy] pyrimidine - the method according to the present invention

a) Obtaining 4-chloro-6[(,,-Cryptor-m-tolyl)oxy] pyrimidine

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To a mixture of m-triptoreline (16.2 g, 0.1 mol) and potassium carbonate (14.5 g, 0,105 mol) in acetone (200 ml) was added 4,6-dichloropyrimidine (14.9 g, 0.1 mol). The reaction mixture was stirred at room temperature for 2 days, was heated under reflux for 3 hours, cooled and poured into water. The resulting aqueous mixture was extracted with methylene chloride. The organic extracts were combined, washed sequentially with 5% sodium hydroxide solution and water, dried over anhydrous magnesium sulfate and concentrated in vacuum, with a specified title product as oil (27.4 g, yield 99%).

b) Obtaining trimethyl 6[(,,-trip is a 27.4 g, 0.1 mol) in toluene (50 l) was added over 10 minutes a solution of trimethylamine in toluene (previously obtained by adding a 27.4 ml liquid trimethylamine to toluene (325 ml) at 0oC. the Reaction mixture was stirred overnight and filtered to obtain a solid substance. The solid is washed with hexane and dried overnight in a vacuum oven at 45-50oWith, receiving specified in the header of the product in the form of not-quite-white solid (23.3 g, yield 70%).

C)Poluchenie-[(,,-Cryptor-4-nitro-m-tolyl)oxy]-6-[(,,-Cryptor-m-tolyl)oxy]pyrimidine

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To the mixture ,,-Cryptor-4-nitro-m-cresol (15,1 g, 0,073 mol) and potassium carbonate (11.3 g, 0,082 mol) in N,N-dimethylformamide 9125 ml) was added trimethyl { 6[(,,-Cryptor-m-tolyl)oxy]-4-pyrimidinyl}ammoniacal (22,8 g, 0,068 mol). The reaction mixture was stirred at room temperature overnight and poured into water. The resulting aqueous mixture was extracted with methylene chloride. The organic extracts were combined, washed sequentially with 5% sodium hydroxide solution, water, 6 N. chloroethanol acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuo, resulting in a yellow solid. Solid is the product in the form of not-quite-white solid (28,2 g, yield 93%).

As you can see from the data in example 4, the method according to the present invention provides for obtaining the target product from 4,6-dichloropyrimidine with the release of 64%.

EXAMPLE 5

Poluchenie-[(,,-Cryptor-4-nitro-m-tolyl)oxy]-6-[(,,-Cryptor-m-tolyl)oxy] pyrimidine - known method using 4,6-giftability

a) Obtaining 4,6-giftability

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A mixture of 4,6-dichloropyrimidine (223,5 g, 1.5 mol), potassium fluoride (279,6 g, 4.8 mol) and tetrabutylammonium (6.0 g, 0,0186 mol) in sulfolane (1 l) was heated at 180-190oWith over 3.5 hours and distilled to receive specified in title product as a colourless liquid (115 g, yield 66%).

b) Obtaining 4-fluoro-6-[(,,-Cryptor-m-tolyl)oxy]pyrimidine

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To a mixture of 4,6-giftability (53,8 g, 0.46 mol) and potassium carbonate (60 g, 0.43 mol) in tetrahydrofuran (700 ml) was added dropwise a solution of m-triptoreline (74,5 g, 0.46 mol) in tetrahydrofuran (300 ml). The reaction mixture was stirred at room temperature for 3 days and poured into water. The resulting aqueous mixture was washed 2 N. a solution of sodium hydroxide and was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and concentrated to the title product in the form of oil (87,4 g, yield 74%).

C)Poluchenie-[(,,-Cryptor-4-nitro-m-tolyl)oxy]-6-[(,,-Cryptor-m-tolyl)oxy]pyrimidine

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A mixture of 4-fluoro-6-[(,,-Cryptor-m-tolyl)oxy] pyrimidine (87,4 g, 0.34 mol),,,, trifter-4-nitro-m-cresol (84,9 g, 0.41 mol) and potassium carbonate (55 g, 0.40 mol) in N,N-dimethylformamide (1 l) was stirred at room temperature until, until the end of the reaction according to the analysis by thin-layer chromatography (hexane-ethyl acetate in the ratio 8: 1). Then the reaction mixture was poured into water and the resulting aqueous mixture was extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate and concentrated in vacuum to obtain a solid substance. The solid is recrystallized from a solution in ethyl acetate-heptane, giving specified in title product as a white solid (108 g, 71% yield).

As you can see from the data in example 5, there is a method using 4,6-giftability, using as starting reagent 4,6-dichloropyrimidine gives obtain the desired product with a yield of 35%.

Thus, the advantage of the method according to the present invention is that it provides a significantly higher yield (64% VM is m

1. The way to obtain unsymmetrical 4,6-bis(aryloxy)-pyrimidine having the structural formula

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where R and R8each independently represents hydrogen or halogen;

R1and R7each independently represents hydrogen, halogen, cyano, nitro, alkyl, halogenated, alkoxy, alkylthio, amino, alkylamino, dialkylamino, alkoxyalkyl, haloalkoxy or alkoxycarbonyl;

R2and R6each independently represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl, haloalkyl, haloalkoxy, alkoxycarbonyl, Gloucestershire, haloalkaliphilic, haloalkaliphilic, nitro or cyano;

R3and R5each independently represents hydrogen, halogen, alkyl or alkoxy; and

R4represents hydrogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl or phenyl;

provided that at least one of R2and R6is not hydrogen and that alloctype not the same; which involves reacting 4,6-developerkeys having the structural formula

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where R4as mentioned above, and X represents CL, Br or I,

with one or less than the molar equivalent of the first phenol, having the cation in the presence of a first solvent to obtain 4-halo-6-(aryloxy)pyrimidine, having the structural formula

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where R, R1, R2, R3, R4and X such as described above;

the interaction of 4-halo-6-(aryloxy)pyrimidine with at least about one molar equivalent WITH1-C4-trialkylamine, in the presence of a second solvent to obtain compounds of ammonium halide having the structural formula

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where R, R1, R2, R3, R4and X such as described above,

Q+is

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where R9, R10and R11each independently represents C1-C4-alkyl;

and the interaction of the compounds of the ammonium halide with at least about one molar equivalent of the second phenol having the structural formula

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where R5, R6, R7and R8such as described above, and the second base in the presence of a third solvent.

2. The method according to p. 1, characterized in that the first and second base selected from the group consisting of a carbonate of an alkali metal, a carbonate of alkaline-earth metal, alkali metal hydride, hydroxide of alkali hydroxide of alkaline-earth metal.

3. The method according to p. 2, in which the first and second base Prout from the group consisting of a simple ester, carboxylic acid amide, halogenated hydrocarbons, sulfoxide and ketone, the second solvent is selected from the group consisting of aromatic hydrocarbons and chlorinated aromatic hydrocarbon, and a third solvent selected from the group consisting of amide carboxylic acid sulfoxide.

5. The method according to p. 1, in which X is CL.

6. The method according to p. 1, in which Q+is

.

7. The method according to p. 1, in which the 4,6-disapperaed interacts with the first phenol and the first base at a temperature of about 0-100oWith a 4-halo-6-(aryloxy)pyrimidine interacts with the amine at a temperature of about 0-100oAnd the connection of the ammonium halide interacts with a second phenol and the second base at a temperature of about 0-100oC.

8. The method according to p. 1, in which R and R8the same and each represents hydrogen or fluorine; R1and R7each independently represents hydrogen, halogen, cyano, nitro or1-C4-alkyl; R2and R6each independently represents hydrogen, fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl,1-C4-haloalkoxy,2- 1-C4-alkyl; and R4represents hydrogen, C1-C4-haloalkyl,1-C4-alkylthio,1-C4-alkylsulfonyl or phenyl.

9. The method according to p. 8, in which:

R, R3, R4, R5and R8represent hydrogen;

one of R1and R7represents hydrogen, chlorine or cyano and the other is fluorine; and

R2and R6represent trifluoromethyl.

10. The compound having the structural formula

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where R represents hydrogen or halogen;

R1represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, alkoxyalkyl, haloalkoxy or alkoxycarbonyl;

R2represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkyl, haloalkyl, haloalkoxy, alkoxycarbonyl, Gloucestershire, haloalkaliphilic, haloalkaliphilic, nitro or cyano;

R3represents hydrogen, halogen, alkyl or alkoxy;

R4represents hydrogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl or phenyl;

X-represents CL-, VG-or I-;

Q+is


 

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in which

R1and R2may be the same or different and mean (C1-C4)-alkyl, and R3means R4-O-, R4-S - or R4R5N-, where R4equal to C1-C4-alkyl, R5means a hydrogen atom, a C1-C4-alkyl or phenyl; 2-N-alkylamino-4,6-dimethoxypyrimidine and method for producing a halogen-substituted pyrimidine

The invention relates to organic chemistry, specifically to new chemical compound 5-hydroxy-3,6-dimethyluracil formula

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showing membrane and antiradical activity

The invention relates to a new method of production (its variants) aminophenylalanine formula I, having the properties of plant growth regulators or herbicides, as well as intermediate products for their production

The invention relates to new sulfonamidnuyu derivatives or their pharmaceutically acceptable salts, which have the properties of inhibitor action of endothelin receptors and can find application in the treatment of diseases associated with disorders in the circulatory system, such as hypertension, ischemia, angina, spasms of the blood vessels as well as to pharmaceutical drugs based on them

The invention relates to new derivatives of arylethanolamine formula I or its pharmaceutically acceptable salts, which have a high affinity for endothelin and can find application in medicine

The invention relates to novel acylated to aminophenylacetylene General formula I which possess herbicide action and selectivity of action in comparison with the previously known compounds of this series

The invention relates to new derivatives of 2-[(2-alkoxy-6-cryptomaterial-4-yl)oxymethylene]phenylacetic acid of General formula I,

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where R is C1-C6-alkyl, R1-halogen, n=0-1, V=0 or NH, U=CH or N

The invention relates to new pyrimidine derivative that exhibit pesticidal activity, in particular fungicidal and insect-acaricidal activity

The invention relates to the field analogues polynucleotides lacking furanose rings

The invention relates to the technical field of herbicides and plant growth regulators, in particular of herbicides for selective control of weeds in cultivated plants

The invention relates to new pyrimidine compounds or their salts with pharmaceutically acceptable acids and pharmaceutical compositions based on them
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