Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using same

A technology of cyanopyrimidine and dimethylaminomethylene, which is applied in the field of continuous preparation of 2-methyl-4-amino-5-cyanopyrimidine and micro-reaction systems, can solve the problems of long reaction time, complicated operation and high energy consumption. The problem of high consumption is to achieve the effect of shortened reaction time, excellent mass and heat transfer, and small reaction volume.

Active Publication Date: 2021-05-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method raw material cost is low, route is simple and simple, but outstanding shortcoming is that (dimethylamine methylene) malononitrile and acetamidine hydrochloride condensation operation are complicated, yield is low (only about 60%), and reaction time is up to 15 ~20 hours and high energy consumption

Method used

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  • Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using same
  • Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using same
  • Micro-reaction system and method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using same

Examples

Experimental program
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Effect test

Embodiment 1

[0076]The methanol solution (200ml) containing sodium methoxide (26.5g, 0.49mol) was cooled to 0°C, and acetamidine hydrochloride (total 46.3g, 0.49mol) was added in batches. After the addition, stir at 0°C for 20min, filter, pour the filtrate into a conical flask, then mix the filtrate with (dimethylaminomethylene) malononitrile (53g, 0.44mol) at a flow rate of 1.12ml / min Methanol solution (350ml) is pumped into the T-type micro-mixer simultaneously with the flow rate of 2.01ml / min (under this condition, the mol ratio of acetamidine hydrochloride and (dimethylaminomethylene) malononitrile is 1:0.92), The temperature in the T-type micro-mixer was controlled to be 55°C, and the two reaction liquids were mixed by the T-type micro-mixer and then directly entered into the Coflore Agitated Cell Reactor (Coflore Agitated Cell Reactor, AMTechnology, UK). The reaction volume inside is 94ml, the vibration frequency is set to 5Hz, the temperature inside the reactor is controlled to 55°C...

Embodiment 2

[0078] This embodiment is the same as Embodiment 1, the only difference is that the temperature inside the T-shaped micro-mixer is controlled to be 35° C. in this embodiment. In this example, the conversion rate of (dimethylaminomethylene) malononitrile was 99%, and the yield of the product 2-methyl-4-amino-5-cyanopyrimidine was 90.4%.

Embodiment 3

[0080] This embodiment is the same as Embodiment 1, the only difference is that the temperature inside the T-shaped micro-mixer is controlled to be 65° C. in this embodiment. In this example, the conversion rate of (dimethylaminomethylene) malononitrile is greater than 99%, and the yield of the product 2-methyl-4-amino-5-cyanopyrimidine is 90.2%.

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Abstract

The invention belongs to the technical field of pharmaceutical engineering, and particularly relates to a micro-reaction system and a method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine by using the micro-reaction system. The preparation method comprises the following steps: respectively and simultaneously pumping an acetamidine hydrochloride solution and a (dimethyl aminomethylene) malononitrile solution into a micro-reaction system comprising a micro-mixer and an oscillating micro-channel reactor which are communicated in sequence, and carrying out a continuous condensation cyclization reaction to obtain the 2-methyl-4-amino-5-cyanopyrimidine. Compared with the prior art, the method has the advantages that the reaction time is shortened to be within 30 minutes, side reactions are inhibited to the maximum extent, the yield of the product 2-methyl-4-amino-5-cyanopyrimidine is increased to 90% or above, operation is easy and convenient, the technological process is continuous, the automation degree is high, the space time yield is high, energy consumption is greatly reduced, cost is low, and industrial application is easy.

Description

technical field [0001] The invention belongs to the field of pharmaceutical engineering, and in particular relates to a micro-reaction system and a method for continuously preparing 2-methyl-4-amino-5-cyanopyrimidine using the same. Background technique [0002] The structural formula of 2-methyl-4-amino-5-cyanopyrimidine (I) is: [0003] [0004] Denoted as compound (I). The compound is a synthetic vitamin B 1 important intermediates. German patent 671787, French patent 819596, Norwegian patent 59015, Swiss patent 193951 and Swiss patent 193952, etc. all describe the synthesis method using malonate as the starting material. In this method, malonate is first reacted with triethyl orthoformate to produce ethoxymethylene malonate, and then condensed with acetamidine hydrochloride to form a ring to generate 2-methyl-4-hydroxy-5-alkoxy ylcarbonylpyrimidine, followed by chlorination, amidation and dehydration to obtain compound (I). This method has many synthesis steps, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42B01J19/28B01J19/00B01F13/00
CPCC07D239/42B01J19/0093B01J19/285B01F33/30
Inventor 陈芬儿姜梅芬程荡黄华山刘敏杰王路路
Owner FUDAN UNIV
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