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Preparation method of 2-amio-4-bromine pyrimidine

A technology of bromopyrimidine and amino, which is applied in the field of preparation of 2-amino-4-bromopyrimidine, can solve the problems of high raw material cost, low reaction yield, poor economic benefit and environmental impact, and reduce raw material cost and The effect of production costs

Active Publication Date: 2017-05-10
SHANGHAI ZAIQI BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As described in the subsequent comparative examples, in the prior art, the synthesis process yield of 2-amino-4-bromopyrimidine is only 16%, and the cost of raw materials is high, the reaction yield is low, and the economic benefits and environmental impact are not good.

Method used

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  • Preparation method of 2-amio-4-bromine pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The first step: the synthesis of 2,4-dibromopyrimidine

[0019] A mixture of phosphorus oxybromide (40.13g, 0.14mol) and uracil (3g, 0.027mol) was stirred at 125°C for 2 hours, the reaction was cooled to room temperature, and the reaction mixture was slowly poured into 500g of ice water, and washed with solid sodium bicarbonate Neutralization reaction. The aqueous phase was extracted twice with 150 ml of dichloromethane. The organic phase was dried and spin-dried under reduced pressure to obtain 6.2 g of crude product, which was purified by flash silica gel column to obtain 5 g of white solid product (yield: 78.5%).

[0020] The second step: the synthesis of 2-amino-4-bromopyrimidine

[0021] 2,4-Dibromopyrimidine (5g, 0.021mol) and ammonia water (28%, 100ml) were stirred at 25°C for 16 hours. After the reaction was completed, the solid was filtered and washed with ether to obtain 3g of crude product. Heating with an oil bath, the crude product was dissolved in metha...

Embodiment 2

[0026] The first step: the synthesis of 2,4-dibromopyrimidine

[0027] A mixture of phosphorus oxybromide (23.22g, 0.081mol) and uracil (3g, 0.027mol) was stirred at 120°C for 2 hours, the reaction was cooled to room temperature, and the reaction mixture was slowly poured into 500g of ice water, and washed with solid sodium bicarbonate Neutralization reaction. The aqueous phase was extracted twice with 150 ml of dichloromethane. The organic phase was dried and spin-dried under reduced pressure to obtain 6 g of crude product, which was purified by column to obtain 4.95 g of white solid product (yield: 77.7%).

[0028] The second step: the synthesis of 2-amino-4-bromopyrimidine

[0029] 2,4-Dibromopyrimidine (5g, 0.021mol) and ammonia in tetrahydrofuran (28%, 100ml) were stirred at 20°C for 16 hours. After the reaction was complete, the solid was filtered and washed with ether to obtain 3g of crude product. Heating with an oil bath, the crude product was dissolved in methanol...

Embodiment 3

[0033] The first step: the synthesis of 2,4-dibromopyrimidine

[0034] A mixture of phosphorus oxybromide (54.18g, 0.189mol) and uracil (3g, 0.027mol) was stirred at 130°C for 2 hours, the reaction was cooled to room temperature, and the reaction mixture was slowly poured into 500g of ice water, and washed with solid sodium bicarbonate Neutralization reaction. The aqueous phase was extracted twice with 150 ml of dichloromethane. The organic phase was dried and spin-dried under reduced pressure to obtain 6.1 g of crude product, which was purified by column to obtain 4.9 g of white solid product (yield: 76.92%).

[0035] The second step: the synthesis of 2-amino-4-bromopyrimidine

[0036] 2,4-Dibromopyrimidine (5g, 0.021mol) and methanolic ammonia solution (28%, 100ml) were stirred at 30°C for 16 hours. After the reaction was complete, the solid was filtered and washed with ether to obtain 3g of crude product. Heating with an oil bath, the crude product was dissolved in metha...

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Abstract

The invention discloses a preparation method of 2-amio-4-bromine pyrimidine; the method takes uracil, phosphorus oxybromide, ammoniation reagent, and others as the raw material; through two-step reactions, the target product 2-amio-4-bromine pyrimidine can be prepared. The preparation method is simple in operation, convenient to purify, high in yield, low in cost, and suitable for industrial scaled production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 2-amino-4-bromopyrimidine. Background technique [0002] 2-Amino-4-bromopyrimidine, aliased as 4-bromo-2-aminopyrimidine; 4-bromopyrimidine-2-amine; 4-bromopyrimidine-2-amino, is an important pharmaceutical intermediate, and its molecular formula is C 4 h 4 BrN 3 . The molecular weight is 173.99866, the simplified structural formula is shown in the following formula 1, and the English name is 4-bromopyrimidin-2-amine. [0003] [0004] As described in the subsequent comparative examples, in the prior art, the synthesis process yield of 2-amino-4-bromopyrimidine is only 16%, and the cost of raw materials is high, the reaction yield is low, and the economic benefit and environmental impact are not good. Contents of the invention [0005] In view of the above-mentioned shortcomings of the prior art, according to the embodiments of the p...

Claims

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Application Information

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IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 王治国宋艳红马秀娟田贝贝李世江李超李强李涛
Owner SHANGHAI ZAIQI BIO TECH
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