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A convenient synthetic method for the preparation of 2-methyl-4-amino-5-aminomethylpyrimidine by one-step cyclization

A technique for the synthesis of aminomethylpyrimidine and its synthesis method, which is applied in the field of convenient synthesis of 2-methyl-4-amino-5-aminomethylpyrimidine, and can solve the difficulty of removing o-chloroaniline, unsatisfactory utilization rate, and consistency requirements High-level problems, to achieve the effects of production protection, saving raw material consumption, and high yield

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

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are relatively mild, but the disadvantage is that the highly carcinogenic o-chloroaniline is used, which is not conducive to environmental protection; and it is difficult to remove the trace amount of o-chloroaniline in the final product vitamin B1
Its disadvantage is that once the acetamidine hydrochloride is neutralized, the free acetamidine is easy to decompose and cannot be stored for a long time, which requires high continuity of the production process, and due to the decomposition of part of the acetamidine, the amount of acetamidine is large and the utilization rate is large. unsatisfactory rate

Method used

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  • A convenient synthetic method for the preparation of 2-methyl-4-amino-5-aminomethylpyrimidine by one-step cyclization
  • A convenient synthetic method for the preparation of 2-methyl-4-amino-5-aminomethylpyrimidine by one-step cyclization
  • A convenient synthetic method for the preparation of 2-methyl-4-amino-5-aminomethylpyrimidine by one-step cyclization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of raw material 3-acylaminopropionitrile

[0039] Take 3-formylaminopropionitrile as an example:

[0040] Add 70 grams (1.0 moles) of 3-aminopropionitrile and 81.4 grams (1.1 moles) of ethyl formate to a 500 milliliter four-neck flask, react at room temperature at 20 ° C, and use gas phase detection to complete the reaction; after the reaction is completed, rectify to obtain 94.1 grams 3-Formylaminopropionitrile, gas phase purity 99.7%, yield 96.0%.

[0041] According to the above-mentioned method, replace the ethyl formate in embodiment 1 with ethyl acetate, n-ethyl propionate, n-butyrate ethyl ester, isobutyrate ethyl ester, ethyl benzoate or o-methylbenzoate ethyl ester respectively, 3-acetylaminopropionitrile, 3-propionylaminopropionitrile, 3-n-propylformylaminopropionitrile, 3-isopropylformylaminopropionitrile, 3-phenylformylaminopropionitrile can be obtained respectively Or 3-o-methylphenylformylaminopropionitrile. Reserve as a raw...

Embodiment 2

[0042] Embodiment 2: The preparation of 2-methyl 4-amino-5-aminomethylpyrimidine, taking 3-formamidopropionitrile as an example, the reaction formula is as follows:

[0043]

[0044] The synthesis steps are as follows:

[0045] Add 360 grams of isopropanol, 98 grams of 3-formamidopropionitrile, 104 grams of acetamidine hydrochloride, and 115 grams of trimethyl orthoformate into a 1000 milliliter glass reaction vessel, stir to dissolve; then add 12.2 grams of anhydrous zinc chloride ; Heating, the internal temperature rose to 85 ~ 90 ° C; stirring the reaction, the use of gas phase detection 3-acetamidopropionitrile reaction is complete.

[0046] After the reaction is completed, cool slightly, add a solution of 90 grams of sodium hydroxide and 200 grams of isopropanol to the obtained reaction liquid, react at 90-95 ° C, and use the liquid phase to detect the conversion of the intermediate until the reaction is completed. The purity and yield of the product 2-methyl-4-amino-5-...

Embodiment 3

[0049] As described in Example 1, the difference is that 112 grams of 3-acetamidopropionitrile is used to replace 98 grams of 3-formamidopropionitrile in Example 1 for the reaction. The preparation steps and conditions are the same as in Example 1, and the resulting product The purity and yield are shown in Table 1.

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Abstract

The invention relates to a portable synthesis method for preparing 2-methyl-4-amino-5-aminoethylpyrimidine through one-step cyclization reaction. The method comprises the following steps: directly catalyzing acetamidine hydrochloride and 3-acyl aminopropionitrile to condense and to react with triester orthoformate for dealcoholization and cyclization by using lewis acid, and then hydrolyzing to obtain a vitamin B1 key intermediate, namely the 2-methyl-4-amino-5-aminoethylpyrimidine. According to the method disclosed by the invention, the raw materials are low in cost and easily obtained, and no sodium alcoholate needs to be used for dissociating acetamidine hydrochloride, thus the decomposition of acetamidine is reduced, and the high yield is achieved through reaction; the cyclization and hydrolysis reactions are sequentially carried out, products in all steps are not required to be separated and purified, and the synthesis method is simple and convenient to operate. Highly carcinogenic o-chloroaniline or other micromolecular aniline compounds are not used, and the portable synthesis method is environment-friendly in process, free of production of wastewater and beneficial to industrial production.

Description

technical field [0001] The invention relates to a convenient synthesis method of 2-methyl-4-amino-5-aminomethylpyrimidine, belonging to the technical field of production of vitamin B1 intermediates and derivatives thereof. Background technique [0002] 2-Methyl-4-amino-5-aminomethylpyrimidine is a key intermediate commonly used in the preparation of vitamin B1. The structural formula is as follows: [0003] [0004] Regarding the synthesis of 2-methyl-4-amino-5-aminomethylpyrimidine in the prior art, there are mainly three traditional routes of cyanopyrimidine, formylpyrimidine and formylaminopyrimidine: route 1, cyanopyrimidine route, Using malononitrile as the starting material, first prepare 2-methyl-4-amino-5-cyanopyrimidine, and then prepare 2-methyl-4-amino-5-aminomethyl by hydrogenation under Raney nickel catalysis pyrimidine. This route needs to use a large amount of ethyl acetimide hydrochloride, which is expensive and unfavorable for product cost reduction. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 戚聿新鞠立柱李新发
Owner XINFA PHARMA
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