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2-amino-4,6-dimethoxypyrimidine synthesis method

A technology for the synthesis of dimethoxypyrimidine and its synthesis method, which is applied in the field of synthesis of 2-amino-4,6-dimethoxypyrimidine, can solve the problems of high operating cost, great environmental hazards, complicated drying equipment, etc. The effect of high efficiency, low moisture control and stable product quality

Active Publication Date: 2018-01-23
YINGKOU YINGXIN CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The structure and synthetic route of 2-amino-4,6-dimethoxypyrimidine have been reported in the literature. At present, 2-amino-4,6-dimethoxypyrimidine uses guanidine nitrate, dimethyl malonate, three Synthesis of raw materials such as phosphorus oxychloride and sodium methoxide. Phosphorus oxychloride is harmful to the environment during transportation and use, and the process is not environmentally friendly; the synthesis of 2-amino-4,6-dimethoxypyrimidine Another route in the method uses malononitrile as a raw material with low cost and environmental friendliness, using malononitrile, methanol, anhydrous hydrogen chloride, toluene, cyanamide, sodium bicarbonate raw materials, intermediate 1,3-dimethylpropane There is absolutely no water in the synthesis process of diamidine dihydrochloride, and anhydrous hydrogen chloride gas is one of the necessary raw materials. However, the preparation of anhydrous hydrogen chloride and drying equipment are complicated, the operating cost is high, and the poor quality of anhydrous hydrogen chloride directly affects the product yield. Rate and other issues

Method used

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Embodiment 1

[0023] The synthetic method of 2-amino-4,6-dimethoxypyrimidine, the steps are as follows:

[0024] (1) Synthesis of 1,3‐dimethylmalonamidine dihydrochloride

[0025] Put 66g of malononitrile and 176g of anhydrous methanol into the reaction kettle, slowly drop 235.5g of acetyl chloride into the kettle, control the reaction temperature at 0-5°C, and add the time for 5 hours. After the addition, continue the insulation reaction for 1 Hour, nitrogen protection filtration, obtains 1,3-dimethylmalonamidine dihydrochloride wet product.

[0026] (2) Synthesis of 3-amino-3-methoxy-N-cyano-2-propionamidine

[0027] Add 1,3‐dimethylmalonimidine dihydrochloride and lye (sodium bicarbonate 20g, sodium hydroxide 30g, water 500g) into the reaction kettle, control the reaction temperature -5-0°C, and slowly add 110g of 50% cyanamide solution, the reaction pH value is 5-6, and the molar ratio of feeding is such that the temperature in the kettle slowly rises to 18°C ​​after the feeding is co...

Embodiment 2

[0032] The synthetic method of 2-amino-4,6-dimethoxypyrimidine, the steps are as follows:

[0033] (1) Synthesis of 1,3‐dimethylmalonamidine dihydrochloride

[0034] Put 66g of malononitrile and 204.8g of anhydrous methanol into the reaction kettle, slowly drop 353.25g of acetyl chloride into the kettle, control the reaction temperature at 10-15°C, and add the time for 8 hours. After the addition, continue the insulation reaction After 2 hours, filter under nitrogen protection to obtain the wet product of 1,3-dimethylmalonamidine dihydrochloride.

[0035] (2) Synthesis of 3-amino-3-methoxy-N-cyano-2-propionamidine

[0036] Add 1,3‐dimethylmalonimidine dihydrochloride and lye (sodium bicarbonate 20g, sodium hydroxide 30g, water 500g) into the reaction kettle, control the reaction temperature at 0-3°C, and slowly add 50 % cyanamide solution 101g, the reaction pH value is 7-8, and the molar ratio of feeding is such that the temperature in the kettle slowly rises to 26° C. after...

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Abstract

The invention provides a 2-amino-4,6-dimethoxypyrimidine synthesis method, which belongs to the technical field of organic synthesis. The invention provides a synthetic route which takes malononitrile, methanol, acetyl chloride, hydrogen cyanamide and alkali liquor as raw materials; the method comprises the following steps of dropwise adding the acetyl chloride to a system of the malononitrile andthe methanol, directly obtaining 1,3-dimethylpropanediamidine dihydrochloride, then reacting with the alkali liquor and the hydrogen cyanamide to obtain 3-amino-3-methoxy-N-cyano-2-propylamidine andfurther performing closed-loop rearrangement to obtain 2-amino-4,6-dimethoxypyrimidine. The synthesis method provided by the invention saves the cumbersome synthesis technology and equipment of the 1,3-dimethylpropanediamidine dihydrochloride, and comprises the steps of adding the acetyl chloride into the malononitrile and the methanol to directly obtain the 1,3-dimethylpropanediamidine dihydrochloride. The synthetic route of the 1,3-dimethylpropanediamidine dihydrochloride in the invention has extremely low moisture control, stable product quality and high yield.

Description

technical field [0001] The invention relates to a synthesis method of 2-amino-4,6-dimethoxypyrimidine, belonging to the technical field of organic synthesis. Background technique [0002] In the development of pesticides, heterocyclic compounds have become the mainstream of research and development of new pesticides. Pyrimidine compounds are an important class of biologically active substances, which are widely used in insecticides, herbicides, fungicides and pharmaceutical intermediates and have attracted people's attention. In the production of sulfonylurea herbicides, 2-amino-4,6-dimethoxypyrimidine is an important intermediate in its synthesis, and there are many varieties of sulfonylurea herbicides prepared from it. [0003] The structure and synthetic route of 2-amino-4,6-dimethoxypyrimidine have been reported in the literature. At present, 2-amino-4,6-dimethoxypyrimidine uses guanidine nitrate, dimethyl malonate, three Synthesis of raw materials such as phosphorus o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
Inventor 刘至寻梁海姜德孜刘子程吴丹黄明辉杨家强王玉
Owner YINGKOU YINGXIN CHEM TECH CO LTD
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