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2-amido pyrimidine production method

The technology of an aminopyrimidine and a production method is applied in the field of preparation of pharmaceutical intermediates, and can solve the problems that 2-aminopyrimidine cannot be satisfied, the reaction yield is low, and the raw materials are difficult to obtain.

Inactive Publication Date: 2006-12-13
HANGZHOU JIANGNAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, in the above-mentioned production method, there are raw materials that are not easy to obtain, the reaction yield is low, etc., and the process is complicated, and the production cost is high, which cannot meet the increasing demand for 2-aminopyrimidine

Method used

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  • 2-amido pyrimidine production method
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  • 2-amido pyrimidine production method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add tetraalkoxymalonal (164.0g, 1.0mol), guanidine hydrochloride (95.g, 1.0mol) and 0.1g sulfonic acid ion exchange resin into a four-necked flask, stir in methanol solvent, and ice salt Cool in a bath to -5°C to 0°C. After 3 hours of cyclization reaction, add 40 g of sodium hydroxide, and distill under reduced pressure to obtain 63.7 g of 2-aminopyrimidine, with a yield of 67.1%.

[0035] Appearance: white crystal

[0036] Melting point: 125℃~126.4℃

[0037] Content (PHLC, area normalization method): 99.48%

Embodiment 2

[0039] Add tetraalkoxymalonal (220.0g, 1.0mol), guanidine hydrochloride (124.2g, 1.3mol) and 0.1g of sulfuric acid ion exchange resin into a four-necked flask, stir in an ethanol solvent, and heat at 10°C to After 5 hours of cyclization reaction at 15°C, 40 g of sodium hydroxide was added, and 87.4 g of 2-aminopyrimidine was obtained after vacuum distillation, with a yield of 91.90%.

[0040] Appearance: white crystal

[0041] Melting point: 124.3℃~125.8℃

[0042] Content (PHLC, area normalization method): 99.53%

Embodiment 3

[0044] Add tetraalkoxymalonal (164.0g, 1.0mol), guanidine hydrochloride (100.3g, 1.05mol) and 10ml hydrochloric acid ion exchange resin into a four-necked flask, stir in methanol solvent, and cool to -5°C ~0°C, reacted for 6 hours, added 40g of sodium hydroxide, and distilled under reduced pressure to obtain 74.4g of 2-aminopyrimidine, with a yield of 78.2%

[0045] Appearance: white crystal

[0046] Melting point: 123℃~126℃

[0047] Content (PHLC, area normalization method): 99.6%

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Abstract

The invention relates the preparing method of 2- amido-pyrimidine, belonging to drug intermediate technology field, comprising the following steps: dissolving the tetraalkoxy- propanedial and guanidine salt in polar solvent, carrying out cyclocondensation reaction with strong acid ion exchange resin as catalyst, neutralizing, carrying out vacuum distillation, and getting 2- amido-pyrimidine. The strong acid ion exchange resin is sulfonic acid ion exchange resin, sulfuric acid ion exchange resin or chlorhydric acid ion exchange resin, the reaction temperature is -5-20Deg.C, and the reaction time is 2-6 hours. The preference temperature and time are -5-0Deg.C and 5-6 hours. The method has the advantages of simple technology, high productivity, high purity and low cost.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, in particular to 2-aminopyrimidine production method. Background technique [0002] 2-aminopyrimidine is an important drug and intermediate for synthesis. The structural formula is: [0003] [0004] It is widely used in the preparation of medicine and pesticide. It is an important intermediate for the synthesis of many agricultural fungicides, sulfonamide herbicides or synthetic analgesics, anticancer drugs and other drugs. However, there are not many synthetic methods for 2-aminopyrimidines, mainly from various substituted aminopyrimidines such as: 4,6-dichloropyrimidine, 4-chloropyrimidine dechlorination by zinc powder reduction, or 2-substituted pyrimidines such as 2- Hydroxypyrimidine to synthesize the product, etc., the main production methods are: [0005] (1) Reductive dechlorination of 4,6-dichloro-2-aminopyrimidine with zinc powder: [0006]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42
Inventor 王列岗
Owner HANGZHOU JIANGNAN CHEM