Preparation method of 2,4-dyhydroxyl-5-pyrimidinecarboxylic acid

A technology of pyrimidinecarboxylic acid and dimethyl methoxymethylenemalonate, which is applied in the field of preparation of important organic synthesis intermediate 2,4-dihydroxy-5-pyrimidinecarboxylic acid methyl ester, and can solve problems such as unpublished , to achieve the effect of easy-to-obtain raw materials, simple operation process and simple post-processing

Inactive Publication Date: 2015-06-03
QUZHOU UNIV
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  • Claims
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Problems solved by technology

At present, there is no published research report on the synthetic ...

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  • Preparation method of 2,4-dyhydroxyl-5-pyrimidinecarboxylic acid
  • Preparation method of 2,4-dyhydroxyl-5-pyrimidinecarboxylic acid

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Embodiment 1

[0018] Synthesis of Dimethyl Methoxymethylene Malonate by Condensation Reaction

[0019] Add 34.8g (0.2mol) of dimethyl methoxymethylenemalonate and 14.4g (0.24mol) of urea into a four-necked flask, add 200mL of ethanol as a solvent, and start stirring to dissolve. Add 3.9g (0.04mol) of sulfamic acid as a catalyst to the four-neck flask, heat and reflux for 5 hours, distill off the solvent, cool, vacuum filter, rinse the filter cake with ice water for several times, at 80°C Dry to constant weight. 25.6 g of white solid ureidomethylene malonate dimethyl was obtained, the yield was 63.37%, m.p.227~230°C.

[0020] Synthesis of methyl 2,4-dihydroxy-5-pyrimidinecarboxylate from ureidomethylenemalonate through ring-closing reaction

[0021] Take 20.2 g (0.1 mol) of ureidomethylene malonate dimethyl ester obtained in the above steps and 160 mL of 10% NaOH solution, heat up to 95 ° C for 2 hours, stop heating, cool to room temperature, and wash with 20% HCl The solution was fir...

Embodiment 2

[0023] Synthesis of Dimethyl Methoxymethylene Malonate by Condensation Reaction

[0024] Add 34.8g (0.2mol) of dimethyl methoxymethylenemalonate and 14.4g (0.24mol) of urea into a four-necked flask, add 200mL of ethanol as a solvent, and start stirring to dissolve. Add 5.8g (0.06mol) of sulfamic acid as a catalyst to a four-neck flask, heat and reflux for 5 hours, distill off the solvent, cool, vacuum filter, rinse the filter cake with ice water for several times, at 80°C Dry to constant weight. 26.5 g of white solid ureidomethylene malonate dimethyl was obtained, the yield was 65.59%, m.p.227~230°C.

[0025] Synthesis of methyl 2,4-dihydroxy-5-pyrimidinecarboxylate from ureidomethylenemalonate through ring-closing reaction

[0026] Take 20.2 g (0.1 mol) of ureidomethylene malonate dimethyl ester obtained in the above steps and 160 mL of 10% NaOH solution, heat up to 95 ° C for 2 hours, stop heating, cool to room temperature, and wash with 20% HCl The solution was first...

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Abstract

The invention discloses a preparation method of 2,4-dyhydroxyl-5-pyrimidinecarboxylic acid. The method comprises the following steps: with ethyl alcohol as a solvent, and methoxy methylene dimethyl malonate and urea as raw materials, adding sulfamic acid as a catalyst, heating, refluxing and carrying out condensation reaction, and distilling to remove an organic solvent; washing and drying to obtain a condensation product; carrying out a ring-closing reaction on the condensation product and a sodium hydroxide solution; and cooling to a room temperature, neutralizing excessive sodium hydroxide with hydrochloric acid, carrying out acidified hydrolysis, filtering, and washing with ice water for a plurality of times, so as to prepare a product 2,4-dyhydroxyl-5-pyrimidinecarboxylic acid. The preparation method disclosed by the invention has the characteristics of being simple in technological operation, cheap and available in raw material, mild in reaction condition, and simple in post-treatment; and the obtained yield can be accepted by industrialized production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of an important organic synthesis intermediate, methyl 2,4-dihydroxy-5-pyrimidinecarboxylate. Background technique [0002] Methyl 2,4-dihydroxy-5-pyrimidinecarboxylate contains multiple functional groups and can be derivatized at multiple positions. It is an important intermediate of the antibacterial drug pipemidic acid and an important intermediate of organic synthesis. The molecular formula of methyl 2,4-dihydroxy-5-pyrimidinecarboxylate is C 6 h 6 o 4 N 2 , the molecular weight is 170, and the molecular structure formula is [0003] [0004] Its appearance is white crystalline powder. At present, there are no public research reports on the synthesis method of methyl 2,4-dihydroxy-5-pyrimidinecarboxylate at home and abroad. Contents of the invention [0005] The purpose of this invention is to provide a kind of preparation...

Claims

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Application Information

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IPC IPC(8): C07D239/557
CPCC07D239/557
Inventor 张彦郑土才
Owner QUZHOU UNIV
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