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Novel technology for synthesis of 5-flucytosine

A technology of flucytosine and new process, applied in the field of synthesizing 5-flucytosine, can solve the problems of difficult procurement, unstable product quality, high price and the like

Inactive Publication Date: 2014-10-08
BEIJING ALLIESYN TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0009] Using 2-methoxy-4-hydroxy-5-fluoropyrimidine, phosphorus oxychloride, and ammonia water as the main raw materials, 5-fluorocytosine is prepared through three steps of chlorination, ammoniation, and hydrolysis. The second step is Ammonia pressurization reaction has potential safety hazards. In addition, the product quality of the final hydrolysis reaction is not stable enough. The amino group on the pyrimidine ring is easily converted into a hydroxyl group, and 2-methoxy-4-hydroxyl-5-fluoropyrimidine is expensive and relatively expensive. Difficult to purchase, high cost of raw materials, close to 300,000 / ton, unstable product quality and many other problems

Method used

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  • Novel technology for synthesis of 5-flucytosine
  • Novel technology for synthesis of 5-flucytosine
  • Novel technology for synthesis of 5-flucytosine

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Embodiment 1

[0020] Add 1500kg of methyl tetrahydrofuran, 180kg of sodium ethoxide, 100kg of acetonitrile and 190kg of methyl formate in sequence in a 3000L reactor, heat up and reflux for 56 hours, cool down to 0-5°C, and set aside. In another 5000L reactor, add 1300kg methyl tetrahydrofuran, 800kg hydrochloric acid ethanol solution, 100kg anhydrous sodium sulfate in sequence, cool down to 0-5°C, add the solution obtained in the previous step into the reactor, dropwise add the process control kettle The internal temperature should not exceed 10°C. After the dropwise addition, raise the temperature to 30-35°C, keep the temperature for 6 hours, cool down to 0-5°C, add baking soda in batches, adjust the pH of the system to be neutral, centrifuge, and rectify the filtrate 230 kg of 3,3-diethoxypropionitrile were obtained. Add 800kg of toluene, 150kg of sodium methoxide and 150kg of urea in the 2000L reactor in sequence, raise the temperature to 60-65°C, keep warm and slowly add 230kg of 3,3-d...

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Abstract

The invention discloses a novel technology for synthesis of 5-flucytosine. The novel technology comprises that through condensation, acidification, cyclisation, fluorination and refining, 5-flucytosine is prepared from acetonitrile, formate, hydrogen chloride low-grade saturated fatty alcohol solution, urea, fluorine gas and anhydrous hydrogen fluoride as main raw materials. The 5-flucytosine has a weight yield of 1.45-1.55 (based on acetonitrile), unknown single impurity content less than 0.1%, total impurity content less than 0.2% and quality satisfying CP2010, USP36 and BP2013 quality standards.

Description

technical field [0001] The invention relates to a new process for synthesizing 5-fluorocytosine, which belongs to the field of pharmaceutical raw materials and pharmaceutical intermediates. Background technique [0002] 5-Fluorocytosine (5-Fluorocytosine), the chemical name is 4-amino-5-fluoro-2(1H)-pyrimidinone. 5-Fluorocytosine has high antifungal activity against Cryptococcus and Candida, and also has high antibacterial activity against Blastomyces, Mycobacterium, some coloring fungi and Aspergillus. This product is antibacterial at low concentration and has bactericidal effect at high concentration. The mechanism of action is to block fungal nucleic acid synthesis. At the same time, 5-fluorocytosine is also a widely used pharmaceutical intermediate, and is a key intermediate for the synthesis of anti-tumor drugs such as flucitabine, emtricitabine, and capecitabine. [0003] Regarding the synthesis of 5-fluorocytosine, there are the following reports: [0004] The syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 吴彬叶华天李青霖
Owner BEIJING ALLIESYN TECH
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