The synthetic method of 2-methyl-4-amino-5-formylaminomethylpyrimidine

A technology for the synthesis of formylaminomethylpyrimidine and its synthesis method, which is applied in the field of synthesis of vitamin B1 and its derivatives, which can solve the problems of long routes and residues, and achieve the effects of eliminating intermediate processes, simple operation, and avoiding trace carcinogen residues

Active Publication Date: 2020-09-01
ZHEJIANG BENLI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Chinese patent CN103012282A discloses using α-sodioformyl-β-formamidopropionitrile II as the starting material, and the steps for synthesizing 2-methyl-4-amino-5-formylaminomethylpyrimidine are three steps: 1) II reacts with hydrogen chloride gas to prepare α-enol-β-formamidopropionitrile; 2) acetamidine hydrochloride is dissociated into acetamidine; 3) α-enol-β-formamidopropionitrile reacts with free acetamidine Amidine cyclization system I. This synthetic method route is long, also needs to use hydrogen chloride and sodium methylate, and the by-product sodium chloride is produced more in the process
However, o-chloroaniline is a carcinogen and will have trace residues in vitamin B1 products

Method used

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  • The synthetic method of 2-methyl-4-amino-5-formylaminomethylpyrimidine
  • The synthetic method of 2-methyl-4-amino-5-formylaminomethylpyrimidine
  • The synthetic method of 2-methyl-4-amino-5-formylaminomethylpyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In the reaction flask, add 500g toluene, 45g solid acid catalyst NbCl 5 / ZrO 2 / SiO 2 , start stirring, slowly add 148.1g of α-sodium formyl-β-formamidopropionitrile, heat up to 65-70°C, start to add dropwise a solution of 105g of acetamidine hydrochloride dissolved in 600g of methanol, after the dropwise addition, continue to keep warm After reacting for 12 hours, 2-methyl-4-amino-5-formylaminomethylpyrimidine reaction solution was obtained. Filtration, recovery of solid acid catalyst NbCl 5 / ZrO 2 / SiO 2 , can be reused after treatment; the filtrate is detected by HPLC, and the yield of 2-methyl-4-amino-5-formylaminomethylpyrimidine is 91.2%.

Embodiment 2

[0024] As described in Example 1, the difference is that the solid acid catalyst NbCl 5 / Al 2 o 3 / SiO 2 instead of solid acid catalyst NbCl 5 / ZrO 2 / SiO 2 Catalyzed reaction was carried out, the preparation steps and conditions were the same as in Example 1, and the obtained yields are shown in Table 1.

Embodiment 3

[0026] As described in Example 1, the difference is that the solid acid catalyst NbCl 5 / ZSM-5 zeolite instead of solid acid catalyst NbCl 5 / ZrO 2 / SiO 2 Catalyzed reaction was carried out, the preparation steps and conditions were the same as in Example 1, and the obtained yields are shown in Table 1.

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Abstract

The invention relates to a synthetic method of 2-methyl-4-amino-5-formyl aminomethylpyrimidine. The method comprises the following steps: a benzene solvent and a solid acid catalyst are added to a reaction flask and stirred, alpha-sodio formyl-beta-formyl aminopropionitrile is added, heating is performed, an acetamidine hydrochloride solution dissolved in an alcohol solvent is added dropwise, a thermal reaction and filtering are performed, the solid acid catalyst is recovered and treated for recycling, and a filtrate is a 2-methyl-4-amino-5-formyl aminomethylpyrimidine solution. O-chloroaniline as a raw material used in the traditional synthetic process is not used, 2-methyl-4-amino-5-formyl aminomethylpyrimidine is directly synthesized from alpha-sodio formyl-beta-formyl aminopropionitrile and acetamidine hydrochloride under the action of the solid acid catalyst, intermediate processes are omitted, the method is an environment-friendly process because the solid acid catalyst is recyclable, and trace cancerogen residues in a vitamin B1 product are avoided; synthesis yield is high, and the requirement for current green development is met.

Description

technical field [0001] The invention relates to a convenient synthesis method of 2-methyl-4-amino-5-formylaminomethylpyrimidine, a key intermediate of vitamin B1, and belongs to the technical field of synthesis of vitamin B1 and its derivatives. Background technique [0002] 2-Methyl-4-amino-5-formylaminomethylpyrimidine is a key intermediate for the synthesis of vitamin B1, the method of synthesizing 2-methyl-4-amino-5-formylaminomethylpyrimidine reported at home and abroad have: [0003] Chinese patent CN103012282A discloses using α-sodioformyl-β-formamidopropionitrile II as the starting material, and the steps for synthesizing 2-methyl-4-amino-5-formylaminomethylpyrimidine are three steps: 1) II reacts with hydrogen chloride gas to prepare α-enol-β-formamidopropionitrile; 2) acetamidine hydrochloride is dissociated into acetamidine; 3) α-enol-β-formamidopropionitrile reacts with free acetamidine Amidine cyclization system I. This synthetic method has a long route and al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42
CPCC07D239/42Y02P20/584
Inventor 徐洪顺吴政杰顾海宁余永志
Owner ZHEJIANG BENLI TECH CO LTD
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