Synthesis method of 2-amino-3-chlorine-5-bromopyrazine

A synthesis method and technology of bromopyrazine are applied in the synthesis field of 2-amino-3-chloro-5-bromopyrazine, can solve the problems of intense reaction, high cost of raw materials, long reaction time and the like, and achieve mild reaction conditions, The effect of stable product quality and easy operation

Inactive Publication Date: 2017-05-10
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of existing 2-aminopyrazine derivatives is cumbersome, the reaction is intense, the impurity content in the product is high

Method used

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  • Synthesis method of 2-amino-3-chlorine-5-bromopyrazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 2-amino-5-bromopyrazine (3.48g, 20mmol), N-chlorosuccinimide (2.67g, 20mmol) and 20ml of methanol into a 50mL single-necked round bottom flask. The mixture in the reaction flask was stirred and reacted at 35°C for 4 hours. TLC confirmed the completion of the reaction. After the reaction, the solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized to obtain the pure product 2-amino-3-chloro-5-bromopyrazine. After drying, the calculated yield was 76.15%, and the purity was 98.42% (HPLC).

Embodiment 2

[0022] Add 2-amino-5-bromopyrazine (3.48g, 20mmol), N-chlorosuccinimide (3.20g, 24mmol) and methanol 20ml into a 50mL single-necked round bottom flask. The mixture in the reaction flask was stirred and reacted at 35°C for 4 hours. TLC confirmed the completion of the reaction. After the reaction, the solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized to obtain the pure product 2-amino-3-chloro-5-bromopyrazine. After drying, the calculated yield was 83.40%, and the purity was 98.75% (HPLC).

Embodiment 3

[0024] Add 2-amino-5-bromopyrazine (52.20 g, 300 mmol), N-chlorosuccinimide (48.07 g, 360 mmol) and 350 ml of acetonitrile into a 1000 mL single-necked round bottom flask. The mixture in the reaction flask was stirred and reacted at 35°C for 4 hours. TLC confirmed the completion of the reaction. After the reaction, the solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized to obtain the pure product 2-amino-3-chloro-5-bromopyrazine. After drying, the calculated yield was 87.00%, and the purity was 99.00% (HPLC).

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Abstract

The invention relates to a synthesis method of 2-amino-3-chlorine-5-bromopyrazine. The synthesis method of the 2-amino-3-chlorine-5-bromopyrazine comprises the following steps: performing reaction on 2-amino-5-bromopyrazine and N-chlorosuccinimide which serve as raw materials under the action of a proper solvent to produce the 2-amino-3-chlorine-5-bromopyrazine, and performing recrystallization to obtain a 2-amino-3-chlorine-5-bromopyrazine pure product. According to the synthesis method of the 2-amino-3-chlorine-5-bromopyrazine, the raw materials are easily available and the price is reasonable; meanwhile, heavy metal and corrosive gas are not used in the preparation reaction, the reaction is mild, special requirements on the reaction equipment are not needed, and the common corrosion-resistant equipment can perform production; the reaction yield is high and the purity is high.

Description

[0001] (1) Technical field [0002] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 2-amino-3-chloro-5-bromopyrazine. [0003] (2) Background technology [0004] 2-aminopyrazine derivatives are the key intermediates of many antineoplastic drugs, such as imidazopyrazines, morpholine imidazopyrazines, and it can be used as synthetic intermediates of organic compounds, such as imidazolidin alkanes substrates. The preparation process of the existing 2-aminopyrazine derivatives is cumbersome, the reaction is intense, the impurity content in the product is high, the output is low, the reaction time is long, and the cost of raw materials is high, which is not conducive to the competitiveness of enterprises. [0005] (3) Contents of the invention [0006] The problem to be solved in the present invention is to provide a synthetic method of 2-amino-3-chloro-5-bromopyrazine which is simple and reasonable in process, low in cos...

Claims

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Application Information

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IPC IPC(8): C07D241/20
CPCC07D241/20
Inventor 耿宣平程伟谈平忠韩猛来新胜来超来子腾
Owner SHANDONG YOUBANG BIOCHEM TECH
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