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Method for synthesizing 5-nbutyl-2-ethylamido-6-methylpyrimidine-4-dimethyl amine sulfonic acid ester

A technology based on dimethyl sulfamate and methyl pyrimidine, applied in 5-n-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethyl sulfamate In the field of synthesis, it can solve the problems of low yield of the original drug, low purity of pyrimol, and low purity of the original drug, and achieve the effect of high purity

Active Publication Date: 2008-11-19
XIAN MODERN CHEM RES INST
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  • Abstract
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  • Application Information

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Problems solved by technology

[0007] The synthesis method disclosed in the above-mentioned patent has the following problems. First, the synthetic yield of the intermediate pyrimol is low, the yield of the crude product is 69.5%, and the content of impurity isomers is high, and the purity of pyrimol is low, so it cannot be directly used for the preparation of Pyrimolsulfonate, it needs to be purified before it can be used as a raw material for preparing pyrithrimolsulfonate
Its two, the yield of the original drug produced is on the low side, and the yield is generally 70%, and the original drug purity is on the low side

Method used

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  • Method for synthesizing 5-nbutyl-2-ethylamido-6-methylpyrimidine-4-dimethyl amine sulfonic acid ester
  • Method for synthesizing 5-nbutyl-2-ethylamido-6-methylpyrimidine-4-dimethyl amine sulfonic acid ester
  • Method for synthesizing 5-nbutyl-2-ethylamido-6-methylpyrimidine-4-dimethyl amine sulfonic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Synthesis of 5-n-butyl-2-nitroamino-6-methylpyrimidin-4-ol

[0026] Add 180.0g (1.0mol) sodium methoxide / methanol solution (30%), 52.0g (0.5mol) nitroguanidine successively in a 1000ml three-necked flask, heat up to reflux, add 112.0g (0.6mol) 2-acetylhexanoic acid Ethyl ester, reflux for 8.0 hours, remove methanol by distillation under reduced pressure, add 300ml of water, stir for 0.5h, let stand for liquid separation, remove the organic layer, neutralize the aqueous layer with 10% hydrochloric acid to pH 5, white precipitate appears, filter to obtain 189.8g filter cake of 5-n-butyl-2-nitroamino-6-methylpyrimidin-4-ol, water content 45%, yield after drying 92.3%, melting point: 159℃~161℃, HPLC Chromatographic (HPLC) content 97.6%.

[0027] 2. Synthesis of pyrithrimol sulfonate

[0028] Add 48.4g (0.8mol) glacial acetic acid, 56.1g (0.8mol, 70%) ethylamine aqueous solution successively in 1000ml there-necked flask, stir at room temperature for 4.0h, add 500ml tolu...

Embodiment 2

[0036] 1. Synthesis of 5-n-butyl-2-nitroamino-6-methylpyrimidin-4-ol

[0037] The step is basically the same as step (1) in Example 1, except that sodium ethoxide / ethanol is used to replace sodium methoxide / methanol, 340.0g (1.0mol) sodium ethoxide / ethanol solution (20%) is added, and the reaction is refluxed for 4.0 hours , ethanol was distilled off under reduced pressure, 300ml of water was added, stirred for 0.5h, the organic layer was removed by static separation, and the aqueous layer was neutralized to pH 8 with 10% hydrochloric acid to obtain 186.4g of 5-n-butyl-2-nitroamine The base-6-methylpyrimidin-4-ol filter cake has a water content of 45%, a yield of 90.7% after drying, and an HPLC content of 95.3%.

[0038] 2. Synthesis of pyrithrimol sulfonate

[0039] The step is basically the same as step (2) in Example 1, and the difference is to replace toluene with xylene, sodium hydroxide to replace sodium carbonate, 5-n-butyl-2-nitroamino-6-methylpyrimidine- The molar r...

Embodiment 3

[0041] 1. Synthesis of 5-n-butyl-2-nitroamino-6-methylpyrimidin-4-ol

[0042] The steps are basically the same as step (1) in Example 1, except that the aqueous layer is neutralized to pH 3 with 10% hydrochloric acid to obtain 195.5g of 5-n-butyl-2-nitroamino-6-methyl The base pyrimidin-4-ol filter cake has a water content of 48%, a yield of 90.0% after drying, and an HPLC content of 96.2%.

[0043] 2. Synthesis of pyrithrimol sulfonate

[0044] Step is basically the same as step (2) in Example 1, and difference is to replace sodium carbonate with potassium carbonate, 5-n-butyl-2-nitroamino-6-methylpyrimidine-4-phenol, glacial acetic acid , ethylamine, acid-binding agent, and N, the molar ratio of N-dimethylsulfamoyl chloride is 1: 3: 3: 0.6: 1.2, and the target product obtained after purification is 106.6g, with a melting point of 47.4°C to 49.7°C, The yield is 84.2%, the GC content is 95.2%, and the total yield is 75.8% based on nitroguanidine as the starting material.

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Abstract

The invention discloses a method for synthesizing 5- normal-butyl-2- ethide amid-6- methyl pyrimidine-4-based dimethyl amine group sulfonic ester (bupirimate). The method takes nitroguanidine and 2-acetyl group ethyl caproate as raw materials which react under the catalytic action of sodium alcoholate to generate 5- normal-butyl-2-nitryl amine-6- methyl pyrimidine-4- phenol which reacts with ethylamine under catalytic action of Glacial acetic acid; and bupirimate is obtained by the reaction of the 5- normal-butyl-2-nitryl amine-6- methyl pyrimidine-4- phenol and N, N-Dimethylsulfamoyl chloride in the presence of alkalescence. The bupirimate prepared by the synthesizing method has the purity quotient up to 95.4 percent, and the total yield coefficient up to 78.6 percent. The method is mainly used to prepare the bupirimate.

Description

technical field [0001] The invention relates to a method for synthesizing 5-n-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate (pyrimolsulfonate). Background technique [0002] Pyrimidine sulfonate is a pyrimidine systemic fungicide developed by ICI. It is prepared by reacting 5-n-butyl-2-ethylamino-6-methylpyrimidin-4-ol (abbreviated as pyrimidine) and dimethylaminosulfonyl chloride. The intermediate pyrimethol itself is a systemic fungicide, which is mainly used for the prevention and treatment of powdery mildew of cereal crops. It is characterized by strong systemic conductivity, resistance to rain erosion, long-lasting effect after application, high efficiency and broad spectrum, suitable for the prevention and control of powdery mildew on fruit trees, vegetables, flowers and other ornamental plants. [0003] Usually the preparation of the intermediate pyrithrimol of pyrithrimol sulfonate is the preparation of pyrithrimol by ethyl guanidine and ethyl 2-acety...

Claims

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Application Information

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IPC IPC(8): C07D239/47A01P3/00
Inventor 丁秀丽李宗英黄晓英徐泽刚宁斌科薛超鲁鸣久
Owner XIAN MODERN CHEM RES INST
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