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Novel synthesis process of 2-substituted-4,6-dialkoxy pyrimidine

A dialkoxypyrimidine and new process technology, which is applied in the field of new synthesis process of 2-substituted-4,6-dialkoxypyrimidine, which can solve the problems of difficult industrial production, harsh operating conditions, easy decomposition and polymerization, etc. problem, to achieve the effect of promoting alcoholysis rate, low production cost and high product purity

Active Publication Date: 2013-06-26
INSIGHT FINECHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But due to the high cost of malononitrile, intermediate dimethoxymalonamidine hydrochloride and substituted cyanamide acid-base and unstable temperature, problems such as easy decomposition and polymerization, so the route has lower yield and lower cost at present. High, relatively harsh operating conditions, difficult to achieve industrial production and other issues

Method used

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  • Novel synthesis process of 2-substituted-4,6-dialkoxy pyrimidine
  • Novel synthesis process of 2-substituted-4,6-dialkoxy pyrimidine
  • Novel synthesis process of 2-substituted-4,6-dialkoxy pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Synthesis of dimethoxymalonamidine hydrochloride

[0042] At room temperature, add malononitrile (132.0g / 2.0mol) and methyl acetate solution (1000ml) of methanol (320.0g / 10.0mol) and solid titanium tetrachloride (2.6g) in a 2L four-necked flask , stir and mix well, pass dry hydrogen chloride gas into the system, keep the pressure of 0.1-0.5MPa, keep the temperature at 25-35°C for reaction and stir for 4 hours, stop the reaction, degas, filter, and dry the filter cake to obtain 436.2g of white solid. Content 91.3% (GC-Area% after derivatization), single-step yield 98.1%, structure by 1 Confirmed by H-NMR.

[0043] (2) Synthesis of hexamethoxypropane

[0044] At room temperature, add dimethoxypropanediamidine hydrochloride (218.1g / 0.98mol) and 1300ml methanol (dried with sodium metal) into a 2L four-neck flask, stir and mix well, and control the pH of the mixture to be 3.5~4, keep warm at 40~45°C for 24 hours, cool down to room temperature, filter and precipitate, ...

Embodiment 2

[0049] (1) Synthesis of dimethoxymalonamidine hydrochloride

[0050] Add malononitrile (132.0g / 2.0mol) and methanol (320.0g / 10.0mol) in methyl acetate solution (1000ml) and zirconium oxide (3.0g) in a 2L four-necked flask, cool to 0~ Stir and mix well at 10°C, pass dry hydrogen chloride gas into the system, keep the pressure of 0.1-0.5MPa, stir for 7 hours, stop the reaction, degas, filter, and dry the filter cake to obtain 417.5g of white solid with a content of 91.9% (derivative GC-Area% after chemical reaction), the single-step yield is 94.5%, and the structure 1 Confirmed by H-NMR.

[0051] (2) Synthesis of hexamethoxypropane

[0052] At room temperature, add dimethoxypropanediamidine hydrochloride (220.9g / 1.0mol) and 1300ml methanol (dried with sodium metal) into a 2L four-neck flask, stir and mix well, and control the pH of the mixture to be 2-3, keep warm at 40-45°C for 31 hours, cool down to room temperature, filter and remove the solvent, add 550ml ethyl acetate to...

Embodiment 3

[0057] (1) Synthesis of dimethoxymalonamidine hydrochloride

[0058] At room temperature, add malononitrile (132.0g / 2.0mol) and methyl tert-butyl ether solution (1000ml) of methanol (320.0g / 10.0mol) and cobalt chloride (1.5g) in a 2L four-necked flask, Stir and mix well, pass dry hydrogen chloride gas into the system, keep the pressure of 0.1~0.5MPa, keep the temperature at 25~35°C for reaction and stir for 5 hours, stop the reaction, degas, filter, and dry the filter cake to obtain 421.0g of white solid, content 92.2% (GC-Area% after derivatization), single-step yield 95.6%, structure 1 Confirmed by H-NMR.

[0059] (2) Synthesis of hexamethoxypropane

[0060] Add dimethoxypropanediamidine hydrochloride (210.5g / 0.96mol) and 1300ml methanol (dried with sodium metal) into a 2L four-necked flask, stir and mix, and control the pH value of the mixture to 3.5-4. Heat the reaction at 20-25°C for 40 hours, filter and remove the solvent, add 550ml of ethyl acetate to the concentrate...

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PUM

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Abstract

The invention relates to a novel synthesis process of 2-substituted-4,6-dialkoxy pyrimidine. The novel synthesis process adopting malononitrile as the raw material and adopting a special solvent comprises the following steps of: obtaining hexaalkoxy propane through imidization and alcoholysis under the action of the special catalyst; carrying out nucleophilic addition onto intermediate and urea / thiourea / guanidine to construct a pyrimidine ring framework; and eliminating and rearranging aromatization to obtain the target compound 2-substituted-4,6-dialkoxy pyrimidine. The synthesis process disclosed by the invention has the characteristics of being cheap and easily available in materials, free of severe conditions for all steps, smooth and safe in operation steps, small in the amount of the three wastes and lower in production cost, and therefore, the synthesis process is suitable for being applied to the industrial production.

Description

technical field [0001] The present invention relates to a synthetic method and a production process of a class of important intermediates of medicine and pesticide 2-substituted-4,6-dialkoxypyrimidine. Under the action, hexaalkoxypropane can be obtained through imidization and alcoholysis, and the intermediate can undergo nucleophilic addition with urea / thiourea / guanidine to complete the construction of the pyrimidine ring skeleton, and then the target series can be obtained through elimination and aromatization rearrangement Compound 2-substituted-4,6-dialkoxypyrimidine, the product purity is greater than 99%, and the total yield is more than 55%. The synthesis method of the present invention has cheap and easy-to-obtain raw materials, all steps have no harsh conditions, and the operation steps are smooth and safe , friendly to the environment, high product purity, low production cost, suitable for industrial production. Background technique [0002] Pyrimidine compounds a...

Claims

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Application Information

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IPC IPC(8): C07D239/52C07D239/60
Inventor 凌云吴清来李永芳薛均陈立柱
Owner INSIGHT FINECHEM
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