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Preparation method of 2-amino-4,6-dichloropyrimidine

A technology of dichloropyrimidine and amino group, which is applied in the field of preparation of 2-amino-4,6-dichloropyrimidine, can solve the problems of high dosage of chlorinating agent, harsh reaction conditions, complicated process, etc. The effect of short cycle and simple processing

Inactive Publication Date: 2022-02-01
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing preparation method is to use guanidinium salt and diethyl malonate to reflux for several hours or longer under the condition of sodium ethoxide or sodium methoxide to synthesize the intermediate 2-amino-4,6-hydroxypyrimidine, and then 2 -Amino-4,6-hydroxypyrimidine is heated and refluxed for several hours under the condition of strong chlorinating agent phosphorus oxychloride to obtain the product 2-amino-4,6-chloropyrimidine; the current preparation method has the following disadvantages, such as: reaction conditions Harsh, complex process, large amount of chlorinating agent, high cost, high energy consumption, low yield

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  • Preparation method of 2-amino-4,6-dichloropyrimidine

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Embodiment 1

[0020] A preparation method of 2-amino-4,6-dichloropyrimidine, comprising the following steps:

[0021] Step 1. Dissolve 5.9g and 100mmol of guanidine hydrochloride, 16.0g and 100mmol of diethyl malonate in 200mL of methanol, then add 20.6g and 150mmol of potassium carbonate, and irradiate for 30min at 25-35°C with a microwave power of 200W Carry out the reaction; then filter the potassium carbonate precipitate, spin the remaining mother liquor to dry the solvent to obtain a white solid, and obtain 13.0 g of the crude product of 2-amino-4,6-hydroxypyrimidine;

[0022] Step 2. Add 13.0 g of 2-amino-4,6-hydroxypyrimidine to 100 mL of oxalyl chloride, irradiate the suspension at 200W microwave power and 35-45°C for 30 minutes to react, spin dry the excess oxalyl chloride to obtain the crude product; Add 60ml of ethyl acetate and heat at 55-65°C until completely dissolved, then cool down to room temperature and add 300ml of petroleum ether, cool down to room temperature and contin...

Embodiment 2

[0032] A preparation method of 2-amino-4,6-dichloropyrimidine, comprising the following steps:

[0033] Step 1. Dissolve 5.9g and 100mmol of guanidine hydrochloride, 16.0g and 100mmol of diethyl malonate in 200mL of methanol, then add 20.6g and 150mmol of potassium carbonate, and irradiate for 30min at 25-35°C with a microwave power of 200W Carry out the reaction; then filter the potassium carbonate precipitate, spin the remaining mother liquor to dry the solvent to obtain a white solid, and obtain 13.0 g of the crude product of 2-amino-4,6-hydroxypyrimidine;

[0034] Step 2. Add 13.0 g of 2-amino-4,6-hydroxypyrimidine to 100 mL of oxalyl chloride, irradiate the suspension at 200W microwave power and 35-45°C for 30 minutes to react, spin dry the excess oxalyl chloride to obtain the crude product; Add 60ml of ethyl acetate and heat at 55-65°C until completely dissolved, then cool down to room temperature and add 300ml of petroleum ether, cool down to room temperature and contin...

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Abstract

The invention discloses a preparation method of 2-amino-4,6-dichloropyrimidine, which comprises the following steps: step 1, dissolving 5.9 g and 100 mmol of guanidine hydrochloride, 16.0 g and 100 mmol of diethyl malonate in 200 mL of methanol, then adding 20.6 g and 150 mmol of potassium carbonate, carrying out a reaction under the conditions that the microwave power is 200 W and the temperature is 25-35 DEG C for 30 min, filtering the potassium carbonate precipitate, and spin-drying the solvent in the residual mother liquor to obtain a white solid, namely 13.0 g of crude 2-amino-4,6-hydroxypyrimidine; and step 2, adding 13.0 g of 2-amino-4,6-hydroxypyrimidine into 100 mL of oxalyl chloride, and irradiating suspension liquid at the microwave power of 200 W and the temperature of 35-45 DEG C for 30 min for reaction. The preparation method of the 2-amino-4,6-dichloropyrimidine is short in reaction period, mild in reaction condition and simple in treatment process, the dosage of a chlorinating agent for synthesis is small, pollution of organic wastewater is greatly reduced, the preparation cost and energy consumption of the 2-amino-4,6-dichloropyrimidine are obviously reduced, the treatment process is simple, and the yield is high.

Description

technical field [0001] The invention relates to the technical field of intermediate synthesis, in particular to a preparation method of 2-amino-4,6-dichloropyrimidine. Background technique [0002] The product 2-amino-4,6-chloropyrimidine is the key intermediate of the antiviral drug famciclovir, which is a new nucleoside spectrum antiviral drug, which is widely used in severe herpes zoster and primary genital herpes, etc. disease. The intermediate 2-amino-4,6-hydroxypyrimidine of the present invention is a pesticide intermediate, which is used for the synthesis of xanthylurea pesticides, such as bensulfuron-methyl, nicosulfuron-methyl, rimsulfuron-methyl, etoxysulfuron-methyl, cyclosulfuron-methyl Propyrimsulfuron and others. [0003] The existing preparation method is to use guanidinium salt and diethyl malonate to reflux for several hours or longer under the condition of sodium ethoxide or sodium methoxide to synthesize the intermediate 2-amino-4,6-hydroxypyrimidine, an...

Claims

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Application Information

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IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 张友杰闫永平胡海威丁靓
Owner ITIC MEDCHEM CO LTD