Method for preparing 2 - amido - 4,6 - dichloro -formamido pyrimidines

A technology of formylaminopyrimidine and aminopyrimidine, which is applied in the field of 2-amino-4, can solve the problems of complex operation, many steps, and low yield, and achieve the solution of complexity and relative harshness, cheap and easy-to-obtain raw materials, and reduce cost effect

Active Publication Date: 2007-07-25
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This route is relatively mature, but there are many steps, and the product obtained by the step-by-step operation is purified and then subjected to the next step of reaction, which makes it difficult to carry out the reaction continuously, and the operation is still relatively complicated
[0008] In summary, the above-mentioned method has the disadvantages of long steps, inconvenient operation, and low yield. Therefore, it is necessary to develop a new method for the synthesis of 2-amino-4,6-dichloro-5-formylaminopyrimidine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 2, the synthesis of 5-diamino-4,6-dihydroxypyrimidine

[0031] Diethyl malonate (32g, 0.2mol), guanidine hydrochloride (9.6g, 0.1mol), sodium ethoxide (27.2g, 0.4mol), ethanol 150mL was heated to reflux, and the solid obtained after the reaction and sodium nitrite (13.8g, 0.2mol) in water 200mL, under the solution of ethanol 170mL and acetic acid 16mL, react at 25 ℃ for 24 hours, the solid obtained after the reaction is in the presence of sodium dithionite (43.5g, 0.25mol) and water 200mL, reflux reaction for 8 hours, 2,5-Diamino-4,6-dihydroxypyrimidine was obtained in 48% yield.

Embodiment 2

[0032] Embodiment 2 2,5-diamino-4, the synthesis of 6-dihydroxypyrimidine

[0033] Diethyl malonate (16g, 0.1mol), guanidine hydrochloride (19.2g, 0.2mol), sodium ethoxide (27.2g, 0.4mol), and 150mL of ethanol were heated to 60°C, and the resulting solid and sodium nitrite (13.8 g, 0.2mol) in water 200mL, ethanol 170mL and acetic acid 16mL solution, heated to reflux for 5 hours, and the solid obtained after the reaction was reacted at room temperature for 48 hours in the presence of sodium dithionite (43.5g, 0.25mol) and water 200mL , to obtain 2,5-diamino-4,6-dihydroxypyrimidine with a yield of 53%.

Embodiment 3

[0034] Example 3 Synthesis of 2,5-diamino-4,6-dihydroxypyrimidine

[0035] Diethyl malonate (64g, 0.4mol), guanidine hydrochloride (9.6g, 0.1mol), sodium methoxide (21.6g, 0.4mol), methanol 150mL was heated to reflux, and the solid obtained after the reaction and sodium nitrite (13.8g, 0.2mol) in the solution of 200mL of water, 170mL of ethanol and 16mL of acetic acid, reacted at 80°C for 8 hours, and the solid obtained after the reaction was reacted at 60°C for 12 hours in the presence of sodium dithionite (43.5g, 0.25mol) and 200mL of water , to obtain 2,5-diamino-4,6-dihydroxypyrimidine with a yield of 78%.

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Abstract

This invention relates to a method for synthesizing 2-amino-4, 6-dichloro-5-formylaminopyrimidine. The method adopts low-cost malonate and guanidine hydrochloride as the starting materials to synthesize 2-amino-4, 6-dichloro-5-formylaminopyrimidine with high efficiency. The method has such advantages as simple process and easy operation.

Description

technical field [0001] The invention relates to a preparation method of 2-amino-4,6-dichloro-5-formylaminopyrimidine. Background technique [0002] AIDS (Acquired Immunodeficiency Syndrome, AIDS for short) is an infectious disease caused by Human Immunodeficiency Virus (Hurman Immunodeficiency Virus, HIV for short). Spread through sexual contact and blood transfusion. AIDS (AIDS) is widely prevalent in the world, has attracted great attention from governments and relevant international organizations, and has become a major public health and social problem. [0003] Since Zidovudine (AZT), the first drug for the treatment of HIV infection / AIDS, was approved by the US FDA in 1987, the research and development of anti-AIDS drugs has advanced by leaps and bounds. At present, more than a dozen drugs have been listed abroad. Among them, Abacavir (Abacavir) is a carbocyclic nucleoside HIV reverse transcriptase inhibitor, the chemical name is (1S, 4R)-4-(2-amino-6-cyclopropylamino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/48
Inventor 姜标赵小龙李阳李帆王万军汪桦
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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