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Method for synthesizing 2-chloropyrimidine

A technology for chloropyrimidine and aminopyrimidine, which is applied in the field of 2-chloropyrimidine preparation and can solve the problems of low yield, low product purity and the like

Inactive Publication Date: 2015-03-25
TAICANG YUNTONG BIOCHEM ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method for synthesizing 2-chloropyrimidine in the prior art has the technical defects that the yield of the substance is low and the product purity is low

Method used

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  • Method for synthesizing 2-chloropyrimidine
  • Method for synthesizing 2-chloropyrimidine
  • Method for synthesizing 2-chloropyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Add 1 mol of tetraalkoxy malonaldehyde, 1.1 mol of guanidinium hydrochloride and 0.1 to 0.2 g of sulfonic acid ion exchange resin into a four-necked flask, stir in isobutanol solvent, and cool to -5°C in an ice-salt bath. After 6 hours of cyclization reaction, sodium hydroxide was added to adjust the pH to 7, and the product 2-aminopyrimidine was obtained after vacuum distillation.

[0017] Add 2.5 mol of hydrochloric acid and 80 g of dichloromethane into a 250 mL reactor, and then add 1 mol of 2-aminopyrimidine under stirring. Add 3.2mol ZnCl at 10~15℃ 2 , After reacting for 30min, a dark yellow suspension was generated. Then it was cooled to -10°C, and 2.4 mol of sodium nitrite was added slowly within 4 hours under the protection of nitrogen. After continuing to feed nitrogen for 1 h, the reaction was terminated. The reactant was poured into 150 mL of water to cool. Separate the liquid, extract the aqueous phase with 40mL dichloromethane for 4-6 times to collect t...

Embodiment 2

[0019] Add 1 mol of tetraalkoxy malonaldehyde, 1.4 mol of guanidinium hydrochloride and 0.1 to 0.2 g of sulfonic acid ion exchange resin into a four-necked flask, stir in isobutanol solvent, cool to 0°C in an ice-salt bath, ring After 2 hours of combined reaction, sodium hydroxide was added to adjust the pH to 8, and the product 2-aminopyrimidine was obtained after vacuum distillation.

[0020] Add 3.5 mol of hydrochloric acid and 80 g of dichloromethane into a 250 mL reactor, and then add 1 mol of 2-aminopyrimidine under stirring. Add 4mol ZnCl at 10~15℃ 2 , After reacting for 60min, a dark yellow suspension was generated. Then cool to 5°C, and add 2.8mol sodium nitrite within 3h under the protection of nitrogen. After continuing to feed nitrogen for 0.5 h, the reaction was terminated. The reactant was poured into 150 mL of water to cool. Separate the liquid, extract the aqueous phase with 40mL dichloromethane for 4-6 times to collect the organic phase, and finally dry al...

Embodiment 3

[0022] Add 1 mol of tetraalkoxy malonaldehyde, 1.3 mol of guanidinium hydrochloride and 0.1 to 0.2 g of sulfonic acid ion exchange resin into a four-necked flask, stir in isobutanol solvent, and cool to -3°C in an ice-salt bath. After 4 hours of cyclization reaction, sodium hydroxide was added to adjust the pH to 7.5, and the product 2-aminopyrimidine was obtained after vacuum distillation.

[0023] Add 3 mol of hydrochloric acid and 80 g of dichloromethane into a 250 mL reactor, and then add 1 mol of 2-aminopyrimidine under stirring. Add 3.5mol ZnCl at 10~15℃ 2 , After reacting for 45min, a dark yellow suspension was generated. Then cool to 0°C, and add 2.5mol sodium nitrite within 3.5h under the protection of nitrogen. After continuing to feed nitrogen for 40 min, the reactant was poured into 150 mL of water to cool. Separate the liquid, extract the aqueous phase with 40mL dichloromethane for 4-6 times to collect the organic phase, and finally dry all the organic phase wi...

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Abstract

The invention discloses a method for preparing 2-chloropyrimidine. According to the method, firstly, tetraalkoxy malonaldehyde and guanidine salt have a cyclization reaction in a polar solvent at the temperature of subzero 5 DEG C-0 DEG C under the catalysis of strong acid action exchange resin serving as a catalyst, pH of a product obtained through the cyclization reaction is adjusted to 7-8, reduced pressure distillation is performed, 2-aminopyrimidine is obtained and is reduced at the temperature of subzero 10 DEG C-5 DEG C under the catalysis of NaNO2, HCl and ZnCl2 serving as catalysts, and a 2-chloropyrimidine product is obtained. By means of the synthetic route, 2-chloropyrimidine with higher purity and higher yield is obtained.

Description

technical field [0001] The invention relates to the technical field of 2-chloropyrimidine preparation, in particular to a method for synthesizing 2-chloropyrimidine. Background technique [0002] 2-Chloropyrimidine, also known as 2-chloropyridoline, has a molecular formula of C 4 h 3 ClN 2 , its molecular weight is 114.53, and its CAS number is 1722-12-9. It is a white or light yellow powder with a melting point of 63-66°C, a boiling point of 75-76°C and a flash point of 98°C. The method for synthesizing 2-chloropyrimidine in the prior art has the technical defects of low yield and low product purity. Contents of the invention [0003] In view of this, the present invention provides a method for synthesizing 2-chloropyrimidine, the product of the synthesis method has higher purity and higher yield. [0004] A method for synthesizing 2-chloropyrimidine, comprising the following steps: [0005] (1) Carry out cyclization reaction of tetraalkoxymalonal (formula A) and gua...

Claims

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Application Information

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IPC IPC(8): C07D239/30
CPCC07D239/30
Inventor 张卫东
Owner TAICANG YUNTONG BIOCHEM ENG
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