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Method for preparing 2,4-dichloro-5-fluoropyrimidine through ultraviolet photocatalytic reaction

A catalytic reaction, fluoropyrimidine technology, applied in the field of medicine and chemical industry, can solve problems such as environmental pollution, and achieve the effects of easy operation, low cost, significant economic and social benefits

Active Publication Date: 2019-05-21
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of the above situation, in order to overcome the defects of the prior art, the purpose of the present invention is to provide a method for preparing 2,4-dichloro-5-fluoropyrimidine by ultraviolet photocatalytic reaction, which can effectively solve the problem of preparing 2,4-dichloro-5-fluoropyrimidine. -5-fluoropyrimidine, and the environmental pollution problem caused by the difficulty of waste acid treatment

Method used

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  • Method for preparing 2,4-dichloro-5-fluoropyrimidine through ultraviolet photocatalytic reaction

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Effect test

Embodiment 1

[0013] The present invention is a method for preparing 2,4-dichloro-5-fluoropyrimidine by ultraviolet photocatalytic reaction, comprising figure 1 As indicated, under ice bath at 0°C, dissolve 15.8 g of 2,4-dimethoxy-5-fluoropyrimidine (II) in 200 ml of dichloroethane solution with stirring, add 0.32 g of sulfuryl chloride, and use high-energy xenon gas to Light the light source, adjust the wavelength of ultraviolet light to 220nm and irradiate for 10 minutes, slowly introduce chlorine gas, control the temperature of the reaction solution at 20-30°C, and the reaction lasts for 12 hours, stop the chlorine, and obtain the reaction solution; add an equal volume of 2,4-dichloro-5-fluoro Pyrimidine (I) 158 g, yield 95%.

Embodiment 2

[0015] A method for preparing 2,4-dichloro-5-fluoropyrimidine by ultraviolet photocatalytic reaction of the present invention is to dissolve 15.8 grams of 2,4-dimethoxy-5-fluoropyrimidine in an ice bath at 0°C under stirring Add 0.7 g of sulfonyl chloride to 200 ml of chloroform solution, use a high-energy xenon lamp light source, adjust the wavelength of ultraviolet light to 260 nm and irradiate for 30 minutes, then slowly introduce chlorine gas, control the temperature of the reaction solution at about 20 ° C, and the reaction lasts for 12 hours. , stop logical chlorine, obtain reaction solution, add equal volume ice water in reaction solution, separate liquid after stirring, organic phase washes with 50 milliliters of 5% sodium carbonate aqueous solution, then washes with 50 milliliters of water, after the organic phase is dried, concentrate under reduced pressure, The pale yellow solid product 2,4-dichloro-5-fluoropyrimidine was 163 grams, and the yield was 98%.

Embodiment 3

[0017] A method for preparing 2,4-dichloro-5-fluoropyrimidine by ultraviolet photocatalytic reaction of the present invention is to dissolve 15.8 grams of 2,4-dimethoxy-5-fluoropyrimidine in an ice bath at 0°C under stirring Add 0.5 g of sulfuryl chloride to 200 ml of dichloroethane solution, use a high-energy xenon lamp light source, adjust the wavelength of ultraviolet light to 300 nm and irradiate for 30 minutes, then slowly introduce chlorine gas, control the temperature of the reaction solution at about 20 ° C, and the reaction continues After 12 hours, stop feeding chlorine to obtain a reaction solution, add an equal volume of ice water to the reaction solution, separate after stirring, wash the organic phase with 50 milliliters of 5% sodium carbonate aqueous solution, then wash with 50 milliliters of water, dry the organic phase and reduce Concentrated under reduced pressure, the light yellow solid product 2,4-dichloro-5-fluoropyrimidine was 151 grams, and the yield was ...

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Abstract

The invention relates to a method for preparing 2,4-dichloro-5-fluoropyrimidine through an ultraviolet photocatalytic reaction. The problem of environmental pollution caused by preparation and waste acid treatment of 2,4-dichloro-5-fluoropyrimidine can be effectively solved. The method comprises the steps that 2,4-dimethoxy-5-fluoropyrimidine is dissolved in a solvent the weight volume of which is10-20 times that of the 2,4-dimethoxy-5-fluoropyrimidine, wherein according to the weight volume, the unit of solids is gram, and the unit of liquid is milliliter; a catalyst sulfuryl chloride is added, and the addition amount of the catalyst sulfuryl chloride is 2-5% of the mass of the 2,4-dichloro-5-fluoropyrimidine; after ultraviolet light irradiation is conducted for 10 minutes, chlorine gasis introduced, the reaction temperature is 15-30 DEG C, and stirring while chlorine introduction is conducted for 12 hours; an equal volume of ice water is added, liquid separation is conducted, an organic phase is washed with an aqueous sodium carbonate solution with the mass concentration of 5%, and water washing, drying and concentration under reduced pressure are conducted to form the solid product 2,4-dichloro-5-fluoropyrimidine. The preparation method is simple, easy to operate, low in cost and free of waste residues, effectively prevents environmental pollution and has significant economic and social benefits.

Description

technical field [0001] The invention relates to medicine and chemical industry, in particular to a method for preparing 2,4-dichloro-5-fluoropyrimidine by using photocatalytic chlorination to prepare 2,4-dichloro-5-fluoropyrimidine by ultraviolet photocatalytic reaction. Background technique [0002] 5-Fluorocytosine is a commonly used anti-infective drug for the treatment of various fungal infections such as cryptococcus and candida. Economic Value. 2,4-dichloro-5-fluoropyrimidine is the key intermediate for the synthesis of 5-fluorocytosine. Its current main production process is to use 5-fluorouracil as raw material and react with the chlorinating agent phosphorus oxychloride at high temperature to prepare have to. Although the preparation method is simple and feasible, a large amount of phosphorus oxychloride is used in the reaction, and a lot of tar-like waste residues are produced at high temperatures. At the same time, a large amount of waste acid is difficult to ha...

Claims

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Application Information

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IPC IPC(8): C07D239/30
Inventor 钟铮杨静张亚萍杨怀霞
Owner HENAN UNIV OF CHINESE MEDICINE
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