Method for synthesizing cytimidine

A technology of cytosine and reactants, which is applied in the field of catalytic synthesis of cytosine, can solve the problems of complex reaction, expensive raw materials, and low yield, and achieve the effects of increasing reaction yield, shortening reaction time, and high yield

Inactive Publication Date: 2009-12-09
上海普渡生化科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The technical problem to be solved by the present invention is to overcome the defects of expensive raw materials, complicated reaction or low yield in the existing technology for synth

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  • Method for synthesizing cytimidine
  • Method for synthesizing cytimidine
  • Method for synthesizing cytimidine

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Experimental program
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Embodiment 1

[0021] In a reaction flask, add 100g of 3-ethoxyacrylonitrile, 300mL of toluene, 200g of sodium methoxide (3.6:1 molar ratio with 3-ethoxyacrylonitrile), 94g of urea (with 3-ethoxyacrylonitrile The molar ratio is 1.5:1), acidic alumina 5g. The reaction mixture was reacted at 70°C, followed by HPLC to stop the reaction after the disappearance of 3-ethoxyacrylonitrile, cooled, added acetic acid to neutralize to pH=7, filtered to obtain a solid mixture, recrystallized with 200g of acetic acid, and recovered the catalyst , to obtain cytosine: mass 90.2g, melting point>280°C, content 99.3% (HPLC, area normalization method), yield 83% (calculated as 3-ethoxyacrylonitrile).

Embodiment 2

[0023] In a reaction flask, add 100g of 3-ethoxyacrylonitrile, 300mL of toluene, 200g of sodium methoxide (3.6:1 molar ratio with 3-ethoxyacrylonitrile), 100g of urea (with 3-ethoxyacrylonitrile The molar ratio is 1.6:1), 0.5 g of acidic alumina, and the reaction mixture was reacted at 70° C., followed by HPLC to stop the reaction after the disappearance of 3-ethoxyacrylonitrile, cooled, added acetic acid to neutralize to pH=7, Filtrate to obtain a solid mixture, recrystallize with 200g of acetic acid, recycle the catalyst, and obtain cytosine: 67g in quality, melting point > 280°C, content 99.3% (HPLC, area normalization method), yield 61.6% (based on 3-ethoxy Acrylonitrile meter).

Embodiment 3

[0025] In a reaction flask, add 100g of 3-ethoxyacrylonitrile, 300mL of toluene, 200g of sodium methoxide (3.6:1 molar ratio with 3-ethoxyacrylonitrile), 96g of urea (with 3-ethoxyacrylonitrile The molar ratio is 1.55:1), 5 g of 3A molecular sieves, the reaction mixture was reacted at 60 ° C, and the reaction was stopped after the disappearance of 3-ethoxyacrylonitrile by HPLC tracking detection, cooling, adding acetic acid to neutralize to pH = 7, and filtering. Obtain a solid mixture, recrystallize with 200 g of acetic acid, recycle the catalyst, and obtain cytosine: quality 98.3 g, melting point > 280 ° C, content 99.3% (HPLC, area normalization method), yield 90.5% (by 3-ethoxypropene Nitrile meter).

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Abstract

The invention discloses a method for synthesizing cytimidine, which comprises the following steps: performing a reaction of a reactant (1) and a reactant (2) to acquire cytimidine under the action of sodium methoxide, wherein the reactant (1) is 3-alkoxy acrylonitrile and/or 3, 3-alkoxy propionitrile, and the reactant (2) is carbamide. The method is characterized in that a solid catalyst is added in the reaction. The catalyst is the solid catalyst, such as one or more of acidic alumina, solid super acid, zinc oxide and a molecular sieve. The method can achieve the effects of shortening the reaction time, improving the yield and reducing the price of raw materials.

Description

technical field [0001] The invention relates to a method for synthesizing cytosine, in particular to a method for catalyzing the synthesis of cytosine. Background technique [0002] Cytosine is an important intermediate in fine chemicals, pesticides and medicine, especially in the field of medicine, mainly used in the synthesis of anti-AIDS drugs and anti-hepatitis B drug lamivudine, anti-cancer drugs gemcitabine, enoxetabine and 5- Flucytosine, etc., are widely used. [0003] The existing cytosine synthesis techniques mainly include the following: [0004] (1) Japanese patents JP58185569 and JP58162579 report the method of preparing cytosine by decarboxylation of cytosine carboxylic acid. The method is simple and convenient, but the raw materials are expensive. Formula 1 is the reaction formula of this method. [0005] [0006] (2) The document "Journal of Biological Chemistry, 1949, 177, 357-360" reported a method of using thiocytosine as a raw material, undergoing ...

Claims

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Application Information

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IPC IPC(8): C07D239/47
Inventor 李宏杰
Owner 上海普渡生化科技有限公司
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