Simple and quick method for synthesizing improved vitamin B1 intermediate 2-methyl-4-amino-5-aminomethylpyrimidine

A technology of formylaminomethylpyrimidine and aminomethylpyrimidine, which is applied in the field of production of vitamin B1 and its derivatives, can solve the problems of difficulty in removing o-chloroaniline, high requirements for the operating environment, and poor reaction selectivity, achieving fewer steps, Effect of reduced decomposition and improved yield

Active Publication Date: 2013-12-11
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the disadvantage of this route 3 is: the use of highly carcinogenic o-chloroaniline requires high operating environment, which is not conducive to environmental protection; and despite steam distillation and repeated recrystal

Method used

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  • Simple and quick method for synthesizing improved vitamin B1 intermediate 2-methyl-4-amino-5-aminomethylpyrimidine
  • Simple and quick method for synthesizing improved vitamin B1 intermediate 2-methyl-4-amino-5-aminomethylpyrimidine
  • Simple and quick method for synthesizing improved vitamin B1 intermediate 2-methyl-4-amino-5-aminomethylpyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: Taking the 3-acetamidopropionitrile of formula (2) as an example, the reaction formula is as follows:

[0063]

[0064] Proceed as follows:

[0065] Preparation of acetamidine free base: add 104.5 g of acetamidine hydrochloride and 220 g of 27 wt% sodium methoxide methanol solution in a 1000 ml glass reaction vessel, react at 10-20°C for 30 minutes, filter, and the filtrate is a methanol solution of acetamidine;

[0066] Add 112 grams of 3-acetamidopropionitrile, 520 grams of toluene, and 27.2 grams of anhydrous zinc chloride into a 1000 ml four-necked flask; heat, and the internal temperature rises to 75-80°C; dropwise add the acetamidine alcohol solution obtained above , the dropping rate is about 10mL / min; the reaction is carried out under stirring conditions, so that the azeotropic removal of water and alcohol is carried out, and the reaction of 3-acetamidopropionitrile is completely detected by gas phase detection. Then add an accurately weighed i...

Embodiment 2

[0070] As described in Example 1, the difference is that 112 grams of 3-acetylaminopropionitrile in Example 1 is replaced with 126 grams of 3-ethylformamidopropionitrile to react, and the preparation steps and conditions are the same as in Example 1. The purity and yield of the obtained product are shown in Table 1.

Embodiment 3

[0072] As described in Example 1, the difference is that 140 grams of 3-n-propylformylaminopropionitrile is used to replace 112 grams of 3-acetylaminopropionitrile in Example 1 to react, and the preparation steps and conditions are the same as in Example 1 , the resulting product purity and yield are shown in Table 1.

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Abstract

The invention relates to a simple and quick method for synthesizing an improved vitamin B1 intermediate 2-methyl-4-amino-5-aminomethylpyrimidine. The method comprises the following steps: condensing 3-alkyl (aryl) formamido-propionitrile serving as a raw material with acetamidine in the catalytic action of lewis acid; cyclizing with trimethyl orthoformate, and hydrolyzing under an alkaline condition to prepare the vitamin B1 key intermediate 2-methyl-4-amino-5-aminomethylpyrimidine. The four reacting processes are performed in sequence by a one-pot reaction, and the product in each step does not need to be separated and purified. According to the method, highly carcinogenic o-chloroaniline or other small molecular aniline compounds are not used, residues of o-chloroaniline compounds in the vitamin B1 product can be eliminated. Furthermore, the preparation process is short and convenient in flow, small in wastewater amount and high in yield.

Description

technical field [0001] The invention relates to a simple and convenient synthesis 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] Vitamin B1, also known as thiamine or antineuritis, is a B vitamin composed of a pyrimidine ring and a thiazole ring. The structural formula is as follows: [0003] [0004] Vitamin B1 has a variety of important physiological functions: it can protect the nervous system, promote gastrointestinal motility, help carbohydrate digestion, improve mental status, maintain normal activity of nerve tissue, muscles, and heart, and vitamin B1 helps to protect the nervous system. Treatment of herpes zoster. The synthesis and preparation of vitamin B1 has attracted much attention, among which 2-methyl-4-amino-5-aminomethylpyrimidine is the key intermediate commonly used for the preparation of vitamin B1. R...

Claims

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Application Information

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IPC IPC(8): C07D239/42
Inventor 侯沧朱成臣鞠立柱汤安于李新发
Owner XINFA PHARMA
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