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Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride

A technology of tetraethylammonium chloride catalyzing the chlorination of pyrimidine ring hydroxy, tetraethylammonium chloride, applied in the direction of organic chemistry, etc., can solve the problems of high pressure of phosphorus oxychloride, large environmental pollution, low catalytic efficiency, etc. Achieve the effect of less environmental pollution, high catalytic efficiency and light color

Inactive Publication Date: 2020-04-03
ANQING BOMAN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the problems of the reported synthesis method of hydroxychlorination of pyrimidine rings, such as heavy environmental pollution, dark color, low catalytic efficiency, and high pressure to recover phosphorus oxychloride, the purpose of the present invention is to provide a new catalytic method for hydroxychlorination of pyrimidine rings

Method used

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  • Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride
  • Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride
  • Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of 4-chloropyrrolopyrimidine

[0050] In a 2L three-neck flask equipped with a thermometer and a condenser, add 184g of phosphorus oxychloride and 16.6g of tetraethylammonium chloride, raise the temperature to 60°C, add 135g of 4-hydroxypyrrolopyrimidine in batches, raise the temperature to 80°C, and keep the temperature for reaction After 30 minutes, the reaction of the raw materials was traced by HPLC, and the temperature was lowered to 30°C.

[0051] Prepare 2 liters of 10% sodium hydroxide solution, slowly add the reaction solution dropwise to extract, and precipitate a solid, filter with suction, and dry to obtain 135 g of the finished product, with a yield of 87.6%.

[0052] 1H NMR (400 MHz, DMSO-ds) δ 12.58 (bs, 1H), 8.58 (s, 1H), 7.69 (d, 1H, J=3.5 Hz), 6.59 (d, 1H, J=3.5 Hz) ppm;

Embodiment 2

[0053] Example 2: Preparation of 2,4-dichloro-7H pyrrole [2,3-D] pyrimidine

[0054] In a 2L three-necked flask equipped with a thermometer and a condenser, add 306g of phosphorus oxychloride and 166g of tetraethylammonium chloride, raise the temperature to 100°C, and add 151g of 2,4-dihydroxy-7H pyrrole [2,3-D ] pyrimidine, the temperature was raised to 110°C, and the temperature was kept for 12 hours, and the reaction of the raw materials was traced by HPLC, and the temperature was lowered to 30°C.

[0055]Prepare 2 liters of 10% sodium hydroxide solution, slowly add the reaction solution dropwise to extract, and precipitate a solid, filter with suction, and dry to obtain 140 g of the finished product, with a yield of 74.5%.

[0056] 1H-NMR (400 MHz, DMSO-d6) ö 12.79 (s, 1H), 7.94 — 7.24 (m, 1H), 6.66(ddd, J= 5.3, 3.5, 1.7 Hz, 1H);

Embodiment 3

[0057] Example 3: Preparation of 2,4-dichloro-7H pyrrole [3,2-D] pyrimidine

[0058] In a 2L three-necked flask equipped with a thermometer and a condenser, add 306g of phosphorus oxychloride and 166g of tetraethylammonium chloride, raise the temperature to 100°C, and add 151g of 2,4-dihydroxy-7H pyrrole [3,2-D ] pyrimidine, the temperature was raised to 110°C, and the temperature was kept for 12 hours, and the reaction of the raw materials was traced by HPLC, and the temperature was lowered to 30°C.

[0059] Prepare 2 liters of 10% sodium hydroxide solution, slowly add the reaction liquid dropwise to extract, and precipitate a solid, filter with suction, and dry to obtain 151 g of the finished product, with a yield of 80.3%.

[0060] 1H NMR (400 MHz, DMSO-d6): δ 6.71 (d, 1H, J=3.2 Hz), 8.09 (d, 1H, J=2.8 Hz), 12.75 (s, 1H, NH).

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Abstract

The invention discloses a preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride, which comprises the following steps: (1) adding phosphorus oxychloride into a container, adding tetraethylammonium chloride as a catalyst, adding a pyrimidine cyclic hydroxyl compound, and heating to react; (2) preparing an alkali liquor, cooling to 0 DEG C, and slowly dropwise adding an obtained reaction liquid into the alkali liquor for quenching to obtain a target product. The method has the advantages that the provided pyrimidine cyclic hydroxyl chlorination catalysis method is small in environmental pollution, the obtained product is light in color, the catalysis efficiency is high, and the phosphorus oxychloride recovery pressure is small.

Description

technical field [0001] The invention relates to the technical field of compound preparation, and more specifically relates to a method for preparing pyrimidine ring hydroxychlorination. Background technique [0002] Pyrimidine is the most common nitrogen-containing heterocyclic compound, which widely exists in organisms[1]. Pyrimidine compounds have strong biological and pharmacological activities and are widely used. [0003] The pyrimidine ring is an important fragment of recent new drugs, such as 4,6-dichloro-5-aminopyrimidine, 2,4-dihydroxypyrrole[2,3-d]pyrimidine, 2-amino-4-chloropyrrolo[2,3 -d]pyrimidine, 4-chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine, 4-amino-7H-pyrrolo[2,3-d]pyrimidine, 5-bromo-7H-pyrrole A[2,3-d]pyrimidine, 2,4,5-trichloro-7H-pyrrole[2,3-D]pyrimidine, 4-chloro-7-tosyl-7H-pyrrole[2,3-D ]pyrimidine, (4-chloro-7H-pyrrolo[2,3-D]pyrimidin-7-yl)methyl pivalate, 4-chloro-5-iodo-7-isopropyl-7H-pyrrolo [2,3-D]pyrimidine, 4-chloro-5-iodo-7H-pyrrolo[2,3-d]py...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/30
CPCC07D239/30
Inventor 陈佳何雪垠刘鹏程
Owner ANQING BOMAN BIOTECHNOLOGY CO LTD
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