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Synthesis method of cytosine

A synthetic method, cytosine technology, applied in the direction of organic chemistry, etc., can solve the problems that it is difficult to meet the economic benefits of large-scale production, the cost of synthesis conditions is difficult to estimate, and there are great difficulties in operation and promotion, so as to facilitate large-scale application , the yield effect is outstanding, and the effect of reducing the loss of solids

Inactive Publication Date: 2014-08-20
NANYANG NORMAL UNIV
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  • Claims
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Problems solved by technology

Although this method improves the product yield to a certain extent, the process operation is complex and cumbersome, the consumption of raw materials is large, the yield improvement rate is small, the cost expenditure is greatly increased, and the cost performance is low, so it is difficult to meet the economic benefits of large-scale production. need
[0007] In 1983, it was proposed that: Add inorganic ammonium salt to the quinoline solution of 5-formylcytosine, heat decarboxylation to obtain cytosine, if necessary, add copper powder or copper-containing compounds (such as: copper sulfate, etc.) to catalyze , the yield is about 60%, but in this method, the specific synthetic conditions have not been reported, and the process cost of the synthetic conditions is difficult to estimate, and there are still great difficulties in actual operation and promotion, and in the following decades , this method has not attracted people's attention

Method used

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preparation example Construction

[0041] The synthetic method of cytosine of the present invention comprises the following steps:

[0042] ①Synthesis of ethyl 3-cyano-2-ureidoacrylate: put the reactants ethyl cyanoacetate, urea, and triethyl orthoformate in a molar ratio of 1.0:1.0~2.0:1.0~2.0, put them into the reaction kettle, and stir After uniformity, heat to reflux and keep warm for 2-4 hours. After cooling to room temperature, a solid precipitated, which was collected, washed with a small amount of acetone, and dried;

[0043] ②Synthesis of 5-ethoxycarbonylcytosine: Add the solid obtained above into the reaction kettle, add solvent, alkali and catalyst, stir evenly, heat to 60~100°C, keep it warm for 2 hours, and precipitate the solid after cooling to room temperature, the obtained Dissolve the solid in water with 3 to 8 times the weight of the obtained solid, add acetic acid to acidify to pH = 7, precipitate the solid, collect the solid, wash with a small amount of acetone, and dry;

[0044] The solve...

Embodiment 1

[0053] The specific synthesis method of intermediate 1 is: in a 2500 ml round bottom flask, add 180 grams (3.0 moles) of urea, 370 grams (2.5 moles) of triethyl orthoformate, 226 grams (2.0 moles) of ethyl cyanoacetate, stir Reflux for 4 hours, and constantly observe the phenomenon of reflux to ensure that the reflux is uniform and stable. After stopping the reaction, cool and filter with suction, collect the yellow-white solid, rinse with acetone, and dry to obtain the intermediate 1 , 294.5 grams of yellow-white powdery solid, the yield is 81%.

[0054] Structural characterization: Proton Magnetic Resonance (HNMR) is carried out with a nuclear magnetic resonance instrument, and the relevant signals of atoms under resonance are recorded as follows:

[0055] 1H NMR (CDCl 3 ,400MHz) δ: 1.35 (3H, t, J =7.2, CH 3 ), 4.25 (2H, q, J =7.2, CH 2 O), 7.65 (1H, br s, NH), 7.83 (1H, br s, NH), 8.19 (1H, s, CH), 11.5 (1H, br s, NH).

Embodiment 2

[0057] The specific synthesis method of intermediate 1 is: in a 2500 ml round bottom flask, add 120 grams (2.0 moles) of urea, 256 grams (2.0 moles) of triethyl orthoformate, 226 grams (2.0 moles) of ethyl cyanoacetate, stir Reflux for 4 hours, and constantly observe the phenomenon of reflux to ensure that the reflux is uniform and stable. After stopping the reaction, cool and filter with suction, collect the yellow-white solid, rinse with acetone, and dry to obtain the intermediate 1 , 305.5 grams of yellow-white powdery solid, the yield is 83%.

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Abstract

The invention discloses a synthesis method of cytosine. According to the method, ethyl cyanoacetate, urea and triethyl orthoformate are utilized as raw materials, ethyl 3-cyano-2-ureido-acrylate, 5-ethoxycarbonyl cytosine, and 5-carboxyl cytosine are sequentially synthesized, decarboxylation is performed to synthesize cytosine and refining, correction, perfection and other various process steps are sequentially performed. Therefore, the yield of the synthesis method is high, the highest total yield can achieve 75.14%, the comprehensive benefits are finally improved and the method has the advantages of simplicity in operation, small difficulty in actual production and convenience in large-scale application.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for synthesizing cytosine. Background technique [0002] Cytosine, white crystalline powder, slightly soluble in water and ethanol, insoluble in ether, melting point 300°C, loses water of crystallization at 100°C, turns brown at 300°C, 320°C; CASNO.71-30-7 , chemical name: 4-amino-2-hydroxypyrimidine, is an important active material involved in the synthesis of DNA and RNA in organisms, and is one of the pyrimidine bases that constitute nucleic acids. Cytosine is an important intermediate in fine chemicals, pesticides and medicine, and has a wide range of applications. In pesticides, it is the first new cytidine peptide antibiotic discovered, which is a broad-spectrum agricultural antibiotic with high efficiency, low toxicity and low residue. In the field of medicine, cytosine is a nucleic acid substance that can be used as an antiviral d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 毛武涛鲍克燕赵强王志强李政道
Owner NANYANG NORMAL UNIV
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