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Preparation process of 3 amino-4 methyl pyridine

A technology of picoline and amino, which is applied in the field of preparation of intermediate 3-amino-4-picoline, can solve the problems of inability to realize industrial production and harsh reaction conditions, and achieve the effect of reducing production cost and high yield

Inactive Publication Date: 2007-07-18
CHINA PHARM UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has a higher yield, the reaction conditions are too harsh to realize industrial production

Method used

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  • Preparation process of 3 amino-4 methyl pyridine
  • Preparation process of 3 amino-4 methyl pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of compound II:

[0020] Add 720ml of 20% oleum and 140g of 4-picoline into the reaction kettle, raise the temperature to 160°C, slowly add 250g of bromine dropwise, react at 160-170°C for 15 hours, cool the reaction liquid to room temperature, pour it into ice water, Adjust the pH to 10-11 with sodium carbonate, and steam distill to obtain 171 g of 3-bromo-4-methylpyridine with a yield of 66%.

Embodiment 2

[0022] Preparation of compound I:

[0023] Add 300ml of methanol, 150g of 3-bromo-4-picoline, 5g of copper sulfate into the autoclave, feed ammonia gas until the pressure reaches 5atm, heat to 160°C, react for 8 hours, cool, filter with suction, and concentrate the filtrate under reduced pressure , the obtained solid was recrystallized from ethyl acetate to obtain 89 g of 3-amino-4-picoline (I), with a yield of 95%.

Embodiment 3

[0025] Preparation of compound I:

[0026] Add 500ml of concentrated ammonia water, 150g of 3-bromo-4-picoline, and 5g of copper sulfate into the autoclave, heat to 180°C after airtight, react for 8 hours, cool, extract 3 times with 500ml of dichloromethane, concentrate under reduced pressure, 84 g of 3-amino-4-picoline (I) was obtained, and the yield was 90%.

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Abstract

This invention relates to the field of pharmaceutical chemistry, involves the preparation method of Intermediate 3-amino-4-methylpyridine (1) of a specific anti-AIDS drugs nevirapine. The feature is it prepared by the 3-halogenated-4-methylpyridine, the preparation method is simple, mild conditions, and the yield is high.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of an intermediate 3-amino-4-picoline (I) of the anti-AIDS drug nevirapine. Background technique [0002] Nevirapine is a non-nucleoside reverse transcriptase inhibitor developed by Boehringer Ingelheim, Germany. This product can bind near the catalytic site of the enzyme, act directly on reverse transcriptase, inhibit its activity, and inhibit HIV replication. It is mainly used to inhibit the mother-to-child virus infection of AIDS in clinical practice. [0003] In EP 393529, US 5569760, its preparation method has been reported in DE 4403311, and their common feature is to use 2-chloro-3-amino-4-methylpyridine as starting material to synthesize nevirapine, so 2-chloro- The synthetic technique of 3-amino-4-picoline has great influence on the total yield and production cost of nevirapine. J.Heterocycl.Chem.; 38; 1; 2001; 99-104. reported that 3-amino-4-pic...

Claims

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Application Information

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IPC IPC(8): C07D213/73
Inventor 黎文海钱方尤启东施忠焕
Owner CHINA PHARM UNIV
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