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Environmentally friendly preparation method of vitamin B1 key intermediate 2-methyl-4-amino-5-aminomethylpyrimidine

A technology of aminomethylpyrimidine and amino group is applied in the production field of vitamin B1 and derivatives thereof, and can solve the problems of unfavorable environmental protection, difficulty in removing o-chloroaniline, and high reaction temperature

Active Publication Date: 2016-04-06
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the weak point of this route 3 is: use highly carcinogenic o-chloroaniline, the operation environment requirement is high, is unfavorable for environmental protection; o-Chloroaniline
The method has high reaction temperature, poor reaction selectivity, low yield, and is difficult to implement industrially

Method used

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  • Environmentally friendly preparation method of vitamin B1 key intermediate 2-methyl-4-amino-5-aminomethylpyrimidine
  • Environmentally friendly preparation method of vitamin B1 key intermediate 2-methyl-4-amino-5-aminomethylpyrimidine
  • Environmentally friendly preparation method of vitamin B1 key intermediate 2-methyl-4-amino-5-aminomethylpyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Embodiment 1: With the functional polymer of 2-aminostyrene of formula (2-1) and sodium enolate as the starting reactant, the reaction formula is as follows:

[0104]

[0105] *: the compound of formula (4) reacts with acetamidine hydrochloride to generate 2-methyl-4-amino-5-formamidomethylpyrimidine (5), and simultaneously releases the functional polymer of aromatic amine structural unit (2-1 ).

[0106] Proceed as follows:

[0107] Add 200 g of water and 150 g of sodium enolate into a 500 ml four-neck flask, stir and dissolve at room temperature to obtain an aqueous solution of sodium enolate.

[0108] In another reactor, add 200 grams of water successively, 178.5 grams (1.5 moles) of formula (2-1) functional polymer (poly-2-aminostyrene) 150 grams of 30% dilute hydrochloric acid, 20 to 25 ℃ insulation reaction 30 minutes; then add the above-prepared aqueous solution of sodium enolate, heat the reaction at 20 to 30 ° C, and use the liquid phase to detect the conv...

Embodiment 2

[0111] The functional polymer (2-1) poly-2-aminostyrene that reclaims with embodiment 1 replaces new poly-2-aminostyrene, gets the polymkeric substance of 178.5 grams of 2-aminostyrene by dry weight, and enol Sodium reaction, the preparation steps and conditions are the same as in Example 1, and the purity and yield of the product obtained are shown in Table 1.

Embodiment 3

[0113] As described in Example 1, the difference is that the functional polymer is selected from formula (2-2) poly-4-aminostyrene, and the number average molecular weight range is 2000 to 12000; replace with 178.5 grams of polymer (2-2) The polymer (2-1) in Example 1 was reacted, and the preparation steps and conditions were the same as in Example 1. The purity and yield of the product obtained are shown in Table 1.

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Abstract

The invention relates to an environment-friendly preparation method for a key intermediate 2-methyl-4-amino-5-aminomethyl pyrimidine of vitamin B1. The method comprises the following steps: substituting highly oncogenic o-chloroaniline or other micromolecular aniline derivatives with a functional polymer containing an aromatic amine structural unit; carrying out a condensation reaction with enol alkali under an acidic condition so as to produce a corresponding enamine polymer; subjecting the enamine polymer and ethanamidine hydrochloride to condensation so as to produce 2-methyl-4-amino-5-formylamino-pyrimidine; and carrying out hydrolysis so as to prepare 2-methyl-4-amino-5-aminomethyl pyrimidine; wherein the functional polymer containing the aromatic amine structural unit is released at the same time and is cyclically used for next batch of reactions. The method has short process flow, discharges a small amount of waste water and waste liquid and is beneficial for industrial production and for improvement of the industrial production level of vitamin B1.

Description

technical field [0001] The invention relates to an environment-friendly preparation method of 2-methyl-4-amino-5-aminomethylpyrimidine, a key intermediate of vitamin B1, and belongs to the technical field of production of vitamin B1 and its derivatives. Background technique [0002] People began to understand and use vitamin B1 very early, and there are relevant records in ancient Chinese medical books, such as the famous doctor Sun Simiao using the bark of rice to treat beriberi. Vitamin B1 is also the first vitamin to be purified by people. In 1896, the Dutch scientist Ekman first discovered vitamin B1. In 1910, the Polish chemist Fonke extracted and purified vitamin B1 from rice bran. The structural formula of vitamin B1 is as follows: [0003] [0004] Vitamin B1, also known as thiamine or antineuritis, is a B vitamin composed of a pyrimidine ring and a thiazole ring. Vitamin B1 is a white crystal or crystalline powder with a weak characteristic odor, bitter taste, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 戚聿新陈军李康艳王涛王海涛鞠立柱李新发
Owner XINFA PHARMA
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