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Chemical synthetic method of 2,4,6-triamido-5-cyano pyrimidine

A technology of cyanopyrimidine and synthesis method, which is applied in the field of chemical synthesis of 2,4,6-triamino-5-cyanopyrimidine, can solve the problems of many route steps, difficult to obtain, not given and the like, and achieves reaction conditions The effect of simplicity, high reaction yield and high product purity

Inactive Publication Date: 2014-11-05
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many route steps in this reaction, and the raw material (N-cyanoimino) dimethyl carbonate is expensive and difficult to obtain, and there is no specific synthetic method of 2,4,6-triamino-5-cyanopyrimidine (CIBA- GEIGY. Process for the preparation of substituted 4,6-dlaminno-5-cyanopyrimidines. WO 95 / 03282)

Method used

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  • Chemical synthetic method of 2,4,6-triamido-5-cyano pyrimidine
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  • Chemical synthetic method of 2,4,6-triamido-5-cyano pyrimidine

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Experimental program
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Effect test

Embodiment 1

[0032] (1) Dissolve 20 g of sodium dicyandiamide in 70 mL of dimethyl sulfoxide solution, stir and dissolve at 120 ° C, and add dropwise 20 mL of dimethyl sulfoxide solution dissolving 15 g of malononitrile in the reaction flask, where The reaction was carried out at high temperature for 5 h, and the reaction process was monitored by TLC. After completion of the reaction, cool to room temperature, wash the slurry with 50 mL of sec-butanol for 30 min, until a light yellow solid is formed, filter with suction, and dry the resulting product in a vacuum oven at 50°C for 5 h to obtain 1-amino-1-cyanoamino-2 ,2-Dicyanoethene sodium salt 26.2g, yield 75%.

[0033] (2) Dissolve 20g of 1-amino-1-cyanoamino-2,2-dicyanoethene sodium salt in 300mL of sec-butanol solution, seal it tightly, introduce hydrogen chloride gas into the mixture, and keep it saturated for 2 hours. The reaction was stirred at ℃ for 18 h, and the reaction process was monitored by TLC. After the reaction was comple...

Embodiment 2

[0036] (1) Dissolve 20g of sodium dicyandiamide in 130mL of N,N-dimethylformamide, stir and dissolve at 160°C, add dropwise 20mL of N,N-dimethylformamide that dissolves 28g of malononitrile into the reaction bottle Formamide solution was reacted at this temperature for 3 h, and the reaction process was monitored by TLC. After completion of the reaction, cool to room temperature, wash the slurry with 50 mL of sec-butanol for 30 min, until a light yellow solid is formed, filter with suction, and dry the resulting product in a vacuum oven at 50°C for 5 h to obtain 1-amino-1-cyanoamino-2 ,2-Dicyanoethene sodium salt 34.5g, yield 99%.

[0037] (2) Dissolve 20g of 1-amino-1-cyanoamino-2,2-dicyanoethene sodium salt in 150mL of sec-butanol solution, seal it tightly, introduce hydrogen chloride gas into the mixture, keep it saturated for 2 hours, 0~5℃ The reaction was stirred for 20 h, and the reaction process was monitored by TLC. After the reaction was completed, the slurry was sucti...

Embodiment 3

[0040] (1) Dissolve 20g of sodium dicyandiamide in 200mL of acetonitrile solution, stir and dissolve at 140°C, add dropwise 10mL of acetonitrile solution in which 15g of malononitrile is dissolved in the reaction flask, react at this temperature for 2h, and monitor the reaction process by TLC . After completion of the reaction, cool to room temperature, wash the slurry with 50 mL of sec-butanol for 30 min, until a light yellow solid is formed, filter with suction, and dry the resulting product in a vacuum oven at 50°C for 5 h to obtain 1-amino-1-cyanoamino-2 ,2-Dicyanoethene sodium salt 24.8g, yield 71%.

[0041] (2) Dissolve 20g of 1-amino-1-cyanoamino-2,2-dicyanoethylene sodium salt in 100mL of methanol solution, seal it, add 50mL of 38% concentrated hydrochloric acid dropwise, stir and react at room temperature for 24h, and monitor the reaction process by TLC . After the reaction was completed, the slurry was filtered with suction, the filter cake was washed with a large ...

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Abstract

The invention belongs to the field of chemical synthesis technology, and in particular relates to a chemical synthetic method of 2,4,6-triamido-5-cyano pyrimidine. The product is an in vitro metabolite of a special in vivo anti-parasitic drug dicyclanil for animals. The invention is characterized in that sodium dicyandiamide and malononitrile as raw materials are subjected to nucleophilic addition reaction to obtain 1-amino-1-cyano-2,2-dicyano sodium acetate, which is then subjected to cyclization in the acidic condition to obtain 2-chloro-4, 6-diamino-5-cyano pyrimidine; and the 2-chloro-4,6-diamino-5-cyano pyrimidine is finally subjected to ammonolysis reaction to obtain the 2,4,6-triamido-5-cyano pyrimidine. The invention has the advantages of reasonable design of synthesis process route, simple operations and high yield.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a chemical synthesis method of 2,4,6-triamino-5-cyanopyrimidine. This product is an in vivo metabolite of dexanil. Background technique [0002] Dicyclanil (Dicyclanil), also known as tripyrrox, with a trade name of Clik, was developed by Ciba-Geigy (currently Novartis) in Switzerland. Dexanil is a novel cyanophagophilic insecticide developed by modifying the structure of cyromazine and a new type of insect growth regulator that is effective by interfering with the formation of parasite epidermis. It has a high killing effect on diptera insects and fleas, and can prevent the larvae of various flies, mites and fleas from developing into pupae or adults. Its insecticidal activity in vitro is more than 10 times that of similar drugs, cyromazine and diflubenuron. Moreover, the drug has the characteristics of single administration, long-lasting drug effect, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/50
CPCC07D239/50
Inventor 袁宗辉赵雅潘源虎王玉莲黄玲利周波陶燕飞陈冬梅谢书宇王旭刘振利谢长清
Owner HUAZHONG AGRI UNIV
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