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Method for preparing 4,6-diamino-2-(cyclopropylamino)-5-pyrimidinecarbonitrile

A cyclopropylamine-based and cyano-pyrimidine technology, which is applied in the field of fine chemical synthesis, can solve the problems of restricting the industrial production and practical application of compounds, the increase of equipment investment and labor input, and the lack of safety and economy, so as to achieve the reduction of production costs and Post-processing input, post-processing simplification, and the effect of safety performance improvement

Inactive Publication Date: 2012-04-04
LIANYUNGANG YAHUI PHARMACHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The extraction, concentration and other operations involved in the reaction operation lead to cumbersome post-processing. These factors make it have high requirements for industrial production equipment in industrial production, and the requirements for process operation are too complicated, and the investment in equipment and labor is increased. Leading to an increase in production costs, there are great deficiencies in safety and economy
These unfavorable factors have all greatly restricted the industrialized production and practical application of this compound

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 500 mL four-necked flask equipped with a mechanical stirrer, a thermometer, and a desiccator, pass N 2 Displace the air. Put in 200 g of absolute ethanol (moisture requirement ≤0.5%), cool down to 10°C with an ice-water bath, then put in 18.8 g of sodium ethoxide (dimethyl dicarbate: sodium ethoxide = 1mol: 1.1mol), and control the temperature at 10-20 Within the temperature range of ℃, 18.2 g of malononitrile (dimethyl dicarboxylate:malononitrile=1mol:1.1mol) and 36.7 g of dimethyl dicarboxylate were added. React at a temperature of 10-20°C for 12-15 hours. Vacuum filtration and drying treatment gave compound (II) 1-methylthio-1-cyanoamino-2,2-dicyanoethene sodium salt. The compound is white solid powder, its content: HPLC≥98%.

Embodiment 2

[0027] In a 500 mL four-necked flask equipped with a mechanical stirrer, a thermometer, and a desiccator, pass N 2 Displace the air. Put in 200 g of absolute ethanol (moisture requirement ≤0.5%), cool down to 10°C with an ice-water bath, then put in 25.6 g of sodium ethoxide (dimethyl dicarbate: sodium ethoxide = 1mol: 1.5mol), and control the temperature at 10-20 Within the temperature range of ℃, 24.9 g of malononitrile (dimethyl dicarbate:malononitrile=1mol:1.5mol) and 36.7 g of dimethyl dicarboxylate were added. React at a temperature of 10-20°C for 12-15 hours. Vacuum filtration and drying treatment gave compound (II) 1-methylthio-1-cyanoamino-2,2-dicyanoethene sodium salt. The compound is white solid powder, its content: HPLC≥98%.

Embodiment 3

[0029] The obtained compound 1-methylthio-1-cyanoamino-2,2-dicyanoethene sodium salt was put into a 1000 mL four-necked flask equipped with a thermometer, a condenser tube, a feeding funnel, and a mechanical stirrer, and 100 g of pure Water, add 263 g refined hydrochloric acid (dimethyl dicarboxylate: HCl=1mol:8mol) dropwise. React at a temperature of 30-40°C for 12 hours, vacuum filter, wash with 100 g of pure water, and then wash with 100 g of 2% Na 2 CO 3 The solution was washed, and the product was dried to obtain 37.5 g of off-white 2-chloro-4-amino-5-cyano-6-methylmercaptopyrimidine, the total yield of two steps was 74.6%, content: HPLC≥95%, m.p.: 267- 268°C.

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Abstract

The invention discloses a method for preparing 4,6-diamino-2-(cyclopropylamino)-5-pyrimidinecarbonitrile, and belongs to the technical field of fine chemical synthesis. The method comprises the following steps of: reacting raw materials, namely N,N-dimethyl-S,S-dimethyl dithiocarbonate, organic alkali metal salt and malononitrile to obtain 1-methylmercapto-1-cyanamide-2,2-dicyano ethylene alkali metal salt, and reacting the compound with hydrochloric acid to obtain 2-chloro-4-amino-5-cyano-6-methylthiopyrimidine; refluxing the 2-chloro-4-amino-5-cyano-6-methylthiopyrimidine and cyclopropylamine in an ethanol solution to obtain 4-amino-2-(cyclopropylamino)-5-cyano-6-methylthiopyrimidine; oxidizing in a dichloromethane solvent by taking acetic acid and urea peroxide as a catalyst system to obtain 4-amino-2-(cyclopropylamino)-5-cyano-6-(methylsulfonyl)pyrimidine; and finally performing substitution by using ammonia water by taking acetonitrile as a solvent to obtain the final product. The method is a synthesis route which is suitable for industrial production and has high economy and operability.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and is a new method for preparing 4,6-diamino-2-cyclopropylamino-5-cyanopyrimidine and its compounds. Background technique [0002] 4,6-Diamino-2-cyclopropylamino-5-cyanopyrimidine, also known as dixinil or pyripridine, code name CGA183893, English chemical name is 4,6-Diamino-2-(cyclo-propyla-min - [0003] o)-5-pyrimidinecarbonitrile is a novel cyano-sucking insecticide disclosed by Ciba-Geigy (now Novartis) in Switzerland in 1994 at the Eighth International Pesticide Chemistry Conference. [0004] The U.S. Patent 4783468 of the people such as Kritinsson provides the preparation method of this compound; preparation. And the preparation method disclosed in the Chinese patent 94192888 published by Swiss Ciba-Geigy company in 1994: (N-cyanoimino) dimethyl carbonate, malononitrile reacts in the methanol solution of sodium methoxide to prepare 1-alkoxy Base-1-cyanoamino-2,2-dicya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/50
Inventor 杨延旗朱建民邱滔罗鸿郁昕
Owner LIANYUNGANG YAHUI PHARMACHEM
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