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Preparation method of uracil

A technology of uracil and ethyl acetate, which is applied in the field of uracil preparation, can solve the problems of limited application range, expensive raw materials and catalysts, etc., and achieve the effects of simple and fast operation, low production cost and high yield

Inactive Publication Date: 2017-07-07
上海旭东海普南通药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Japanese patent JP2001151761 discloses a preparation method of uracil, which uses cyanoacetyl urea to synthesize uracil through condensation reaction and palladium carbon catalytic reduction. The raw materials and catalyst used in this method are relatively expensive, which limits the scope of application of the reaction.

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  • Preparation method of uracil
  • Preparation method of uracil
  • Preparation method of uracil

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add sodium methoxide (4.32g, 0.08mol) and ethyl acetate (0.13mol, 12.5mL) into a 50mL reaction flask, stir at room temperature for 10min, slowly add ethyl formate (0.05mol, 4.1mL) dropwise, and complete the dropwise addition in 30min . Transfer to a 35°C oil bath to continue the reaction. The system dissolves first, and a large amount of white solids are produced after a period of time. After 4 hours, GC-MS detected that the ethyl formate was completely reacted, and it was directly used in the next reaction without separation.

Embodiment 2

[0023] Weigh thiourea (0.045mol, 3.42g), grind it and add it to the crude product obtained in Example 1, the reaction solution becomes viscous, add 15mL of ethyl acetate to dilute the reaction system, stir and react at 60°C for 2 hours, TLC detects the reaction Finish. Concentrate the reaction solution to dryness, add 40 mL of hydrochloric acid solution (3mol / L) to the obtained white solid to make a slurry for 1 hour, then suction filter, rinse the filter cake with 10 mL of water, and dry it in vacuum at 50°C for 4 hours to obtain 4.25 g of white solid powder, two The combined yield is 74%, and the purity is 98.97%.

[0024] 1 H NMR (400MHz, DMSO) δ12.43(s, 1H), 12.26(s, 1H), 7.41(d, J=7.5Hz, 1H), 5.82(d, J=7.6Hz, 1H).

Embodiment 3

[0026] Add thiouracil (4.15g, 0.033mol), potassium hydroxide (2.79g, 0.05mol) and 30mL ethanol to a 100mL reaction flask, cool to 0‐5°C, slowly add 30% Wt H2O2 (10.2ml, 0.1 mol), after the dropwise addition was completed, it was transferred to an oil bath at 60°C and stirred for 4 hours. After the reaction was detected by TLC, it was cooled to room temperature and filtered with suction, and the filter cake was washed with 5 mL of ethanol. Add 15mL of water to the obtained off-white solid and stir evenly, then slowly add 4.5mL of concentrated hydrochloric acid dropwise, transfer to an oil bath at 60°C and stir for 1 hour after the dropwise addition is completed, after the system is cooled to room temperature, suction filter, and the filter cake is washed with 5mL of cold water , the obtained white powder was dried in vacuum at 50° C. for 5 hours to obtain 2.37 g of white powdery solid, yield: 65.3%, purity 99%.

[0027] 1 H NMR (400 MHz, DMSO) δ 10.97 (s, 1H), 10.78 (s, 1H), 7...

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Abstract

The invention discloses a preparation method of uracil. The method comprises the following steps: (a) enabling ethyl formate, ethyl acetate and sodium methylate to react so as to prepare sodium (E)-3-ethoxy-3-oxoprop-1-en-1-olate; (b) adding thiourea and ethyl acetate into the sodium (E)-3-ethoxy-3-oxoprop-1-en-1-olate, heating for carrying out a reaction, and acidizing by using hydrochloric acid to obtain thiouracil; (c) adding alkali and ethanol into the thiouracil, cooling and then dropwise adding a hydrogen peroxide water solution into the cooled mixture; after that, heating for carrying out a reaction to obtain the uracil. According to the technology for preparing the uracil by using the thiourea as a raw material, the used raw materials such as ethyl formate, the ethyl acetate, the thiourea and hydrogen peroxide are chemical products which are common, easy to obtain and low in price, so that the production cost is lower. The preparation method of the uracil is simple, convenient and fast to operate and high in yield, thus being suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of uracil. Background technique [0002] Uracil is an organic base, which is an important intermediate in the synthesis of antineoplastic drugs 5‐fluorouracil, tegafur, doxifluridine and antiviral drugs 5‐iodo‐2'‐deoxyguanosine, etc. Organic Synthesis. Japanese patent JP2001151761 discloses a method for preparing uracil, which uses cyanoacetyl urea to synthesize uracil through condensation reaction and palladium carbon catalytic reduction. The raw materials and catalyst used in this method are relatively expensive, which limits the scope of application of the reaction. Contents of the invention [0003] The purpose of the present invention is to provide a method for preparing uracil with low raw material cost, simple and safe operation and easy large-scale production. [0004] Technical solution of the present invention is: [0005] In the first step, ethyl acetate and ethyl formate undergo a nucleophi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCC07D239/54
Inventor 符爱清马明亮张春
Owner 上海旭东海普南通药业有限公司
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