Synthesizing method of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine

A technology of dimethoxyl and synthetic methods, applied in the field of synthesis of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine, It can solve the problems of low yield and achieve the effect of simple operation, mild reaction conditions and little irritation

Inactive Publication Date: 2013-08-07
HEILONGJIANG UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the technical problem that the method yield of existing preparation 2-amino-5,8-dimethoxy [1,2,4]-triazolo[1,5-c]-pyrimidine is low , providing a synthetic method of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine

Method used

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specific Embodiment approach 1

[0033] Specific embodiment one: The synthesis method of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine in this embodiment is as follows:

[0034] One, the synthesis of 3-hydroxyl-2-methoxymethyl acrylate sodium salt:

[0035] Mix 400ml of tetrahydrofuran with 29.0g of alkali, cool in an ice-water bath to 5°C, and then add dropwise a mixture of 67.4g of methyl methoxyacetate and 48.0g of methyl formate at 10°C to 20°C. Reaction under the condition of ℃-20℃ for 5h, and then remove the solvent under reduced pressure to obtain 3-hydroxy-2-methoxymethyl acrylate sodium salt;

[0036] Two, the synthesis of 2-mercapto-5-methoxy-4-hydroxypyrimidine:

[0037] Add 3-hydroxy-2-methoxymethyl acrylate sodium salt into 300ml of methanol, then add 48.0g of thiourea and 50.0g of alkali, reflux for 12 hours, drop to room temperature, remove the solvent by rotary evaporation, add 300ml of water, wash with hydrochloric acid Adjust the pH value to 3-4, filter, wash with water, and dry ...

specific Embodiment approach 2

[0052] Embodiment 2: The difference between this embodiment and Embodiment 1 is that the sodium hydroxide solution described in step 3 is prepared by dissolving 32.6g of sodium hydroxide in 620ml of water. Others are the same as in the first embodiment.

specific Embodiment approach 3

[0053] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that the aqueous sodium bicarbonate solution described in step six is ​​prepared by dissolving 32g sodium hydroxide in 500ml water. Others are different from the first or second specific embodiment.

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Abstract

The invention relates to a synthesizing method of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine. The invention solves the problems such as low yield, high pollution, complicated operation, and the like of current preparation methods. The method provided by the invention comprises the steps that: methoxy methyl acetate and methyl formate are condensed under a strong-alkali condition; the condensation product is subjected to cyclization with thiourea; methylation is carried out by using chloromethane; chlorination is carried out by using phosphorus oxychloride; hydrazination is carried out by using hydrazine hydrate; the product is subjected to cyclization with cyano bromine; and under the effect of strong alkali and acrylate, a final product is obtained. With the method provided by the invention, the yield of each step is higher than 80%, and a total yield reaches 39%. The method is suitable for industrialized productions. The method provided by the invention belongs to the field of paddy rice herbicide penoxsulam intermediate preparation.

Description

technical field [0001] The invention relates to a method for synthesizing 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine. Background technique [0002] 2-Amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine is the key intermediate of penoxsulam, an ultra-efficient paddy field herbicide, five Flusulam is a broad-spectrum herbicide for paddy fields that was registered by Dow AgroSciences in 2004, promoted in 2005, and entered the Chinese market in 2008. And a variety of broad-leaved grasses have good control effect. With the continuous manifestation of the superior performance of penoxsulam, people's demand for penoxsulam continues to increase, so it is of great significance to study its intermediates. [0003] For the synthesis of 2-amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-c]-pyrimidine, the most common method is methyl 2-methoxyacetate As the starting material, it is condensed with methyl formate under the action of sodium methoxide to obtain the sodium salt of 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 高金胜周金枝牛立中姚林山宫炜
Owner HEILONGJIANG UNIV
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