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Preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine

A kind of methyl pyrimidine, ethyl amino technology, applied in the field of preparation of 5-n-butyl-2-ethyl amino-4-hydroxy-6-methyl pyrimidine, can solve the problem of unsuitable for industrial production, use to Dimethyl sulfate, unpleasant smell, mercaptan and other problems, to achieve the effect of broad industrial application prospects, improved yield and simple separation

Active Publication Date: 2021-04-20
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The problem with this method is that highly toxic dimethyl sulfate is used in the reaction process, which poses a great potential safety hazard.
In addition, the process will not only generate bad-smelling mercaptans, but also pollute the environment, which is not suitable for industrial production

Method used

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  • Preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine
  • Preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine
  • Preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine

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Experimental program
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Effect test

Embodiment 1

[0033] (1) In a 100ml four-neck flask equipped with a stirrer, a thermometer, and a condenser tube, add 10g of concentrated sulfuric acid dropwise to 19.3g of ethylamine aqueous solution (70%), react for 30min, then add 10ml of methanol and 16.8g of cyanamide aqueous solution (50%) was stirred at 30°C for 4h to generate N-ethylguanidine sulfate, which was suction filtered and dried to obtain N-ethylguanidine sulfate with a yield of 72% and a purity of 96%.

[0034] (2) Mix 10.4g of N-ethylguanidine sulfate, 3.1g of sodium hydroxide and 50ml of toluene in a 100ml four-neck flask equipped with a stirrer, a thermometer, and a condenser, and add 13.0g of 2- Ethyl n-butyl acetoacetate, after heat preservation for 1 hour, add sulfuric acid to adjust the pH to neutral, stir, and filter with suction to obtain isomer 2-amino-5-n-butyl-3-ethyl-6-methyl -The crude product of 4(3H)-pyrimidinone, through the preparative chromatography of acetonitrile / water with a mobile phase volume ratio ...

Embodiment 2

[0036] (1) In a 100ml four-neck flask equipped with a stirrer, a thermometer, and a condenser tube, add 10g of concentrated sulfuric acid dropwise to 19.3g of ethylamine aqueous solution (70%), react for 30min, then add 10ml of ethanol and 16.8g of cyanamide aqueous solution (50%) was stirred at 30°C for 4h to generate N-ethylguanidine sulfate, which was suction filtered and dried to obtain N-ethylguanidine sulfate with a yield of 69% and a purity of 96%.

[0037] (2) In a 100ml four-necked flask equipped with a stirrer, a thermometer and a condenser tube, mix 10.4g of N-ethylguanidine sulfate, 3.1g of sodium hydroxide and 50ml of toluene, and add 13.0g of 2 -Ethyl n-butyl acetoacetate, after insulation reaction for 1h, add sulfuric acid to adjust the pH to neutral, stir, and filter with suction to obtain isomer 2-amino-5-n-butyl-3-ethyl-6-methyl The crude product of base-4(3H)-pyrimidinone is obtained through the preparative chromatography of acetonitrile / water with a mobile ...

Embodiment 3

[0039] (1) In a 100ml four-neck flask equipped with a stirrer, a thermometer, and a condenser tube, add 10g of concentrated sulfuric acid dropwise to 16.7g of ethylamine aqueous solution (70%), react for 30min, then add 10ml of ethanol and 16.8g of cyanamide aqueous solution (50%) was stirred at 30°C for 4h to generate N-ethylguanidine sulfate, which was suction filtered and dried to obtain N-ethylguanidine sulfate with a yield of 67% and a purity of 95%.

[0040] (2) In a 100ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, mix 10.4g of N-ethylguanidine sulfate, 3.7g of sodium hydroxide and 50ml of toluene, and add 13.0g of 2 -Ethyl n-butyl acetoacetate, after insulation reaction for 1h, add sulfuric acid to adjust the pH to neutral, stir, and filter with suction to obtain isomer 2-amino-5-n-butyl-3-ethyl-6-methyl The crude product of base-4(3H)-pyrimidinone is obtained through the preparative chromatography of acetonitrile / water with a mobile phas...

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Abstract

The invention discloses a preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine, which comprises the following steps: by using ethylamine and cyanamide as initial raw materials, generating N-ethylguanidine sulfate under the action of concentrated sulfuric acid, reacting with 2-n-butyl ethyl acetoacetate under the action of sodium hydroxide for 1-4 hours, and carrying out after-treatment to obtain 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine. According to the method, cheap and easily available ethylamine and cyanamide are used as initial raw materials, the method is green and environment-friendly, isomers are separated by using a preparative chromatography technology, the yield and purity of the product are relatively high, and the method has a wide industrial application prospect.

Description

technical field [0001] The invention relates to a preparation method of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine, which belongs to the technical field of organic synthesis chemistry. Background technique [0002] 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine, English common name ethirimol, structural formula is: 5-n-Butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine is a systemic pyrimidine fungicide used to control powdery mildew in crops such as apples, greenhouse roses and strawberries, the color is White solid powder, precisely because of the excellent characteristics of 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine, it has been widely used in the field of medicine and polymer fields. The annual market demand for 5-n-butyl-2-ethylamino-4-hydroxy-6-methylpyrimidine is far greater than the supply, and the synthesis of 5-n-butyl-2-ethylamino-4-hydroxy The new method of -6-methylpyrimidine has been a research hotspot for chemists. The production techn...

Claims

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Application Information

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IPC IPC(8): C07D239/47
Inventor 李斌栋宋国盛候静
Owner NANJING UNIV OF SCI & TECH