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Synthesis method of 2-amino-6-chloropurine

A synthesis method and chloropurine technology, applied in directions such as organic chemistry, can solve the problems of unstable thioguanine, low product yield, environmental pollution, etc., and achieve the effects of being suitable for popularization and application, high yield, and few by-products

Inactive Publication Date: 2018-05-29
ZHONGSHAN DEGAOXING INTPROP CENT LLP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its main synthetic routes are as follows: one is to use guanine to react with phosphorus pentasulfide, and then to react with chlorine to make it. This method has a strong smell, pollutes the environment, and thioguanine is unstable; Phosphorus is directly chlorinated and then hydrolyzed under the phase transfer catalyst tetramethylammonium chloride. This method has low product yield due to the low solubility of guanine, and a large amount of expensive phase transfer catalyst is used. For this reason, we propose A kind of synthetic method of 2-amino-6-chloropurine is put into use to solve the above problems

Method used

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  • Synthesis method of 2-amino-6-chloropurine

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Embodiment 1

[0019] A kind of synthetic method of 2-amino-6-chloropurine, the concrete steps of this synthetic method are as follows:

[0020] S1: Add 200ml of 1,2-dichloroethane, 40ml of tetrahydrofuran and 20g of guanine into a dry reaction flask, add 30ml of phosphorus oxychloride dropwise at 20°C, and keep stirring for 1 hour after the addition is complete. The dropwise addition of phosphorus oxychloride is completed within 10 minutes;

[0021] S2: Then heat up to reflux reaction. After the reaction is completed, add 1g of developer to the reaction solution and drop it into 300ml of the mixed solution. React for 1h. Cool it to 10°C with ice water. After filtering, a solid reactant is obtained. The temperature of the temperature rise and reflux reaction is 40 °C, the reaction time is 4h, the mixed solution is a mixture of tetraethylammonium chloride and acetonitrile anhydrous, wherein tetraethylammonium chloride: acetonitrile anhydrous=1:5;

[0022] S3: Mix the solid reactant with 100 ...

Embodiment 2

[0026] A kind of synthetic method of 2-amino-6-chloropurine, the concrete steps of this synthetic method are as follows:

[0027] S1: Add 300ml of 1,2-dichloroethane, 60ml of tetrahydrofuran and 30g of guanine into a dry reaction flask, add 40ml of phosphorus oxychloride dropwise at 30°C, and keep stirring for 1~ 3h, the dropwise addition of phosphorus oxychloride is completed within 15min;

[0028] S2: Then heat up to reflux reaction. After the reaction is completed, add 1~3g developer to the reaction solution and drop it into 500ml of the mixed solution. React for 3 hours. Cool it to 15°C with ice water. After filtering, obtain a solid reactant. The temperature is 60°C, the reaction time is 6h, the mixed solution is a mixture of tetraethylammonium chloride and anhydrous acetonitrile, wherein tetraethylammonium chloride:anhydrous acetonitrile=1:5;

[0029] S3: Mix the solid reactant with 200ml of 12% acetic acid solution and react at 80° C. for 2 hours. After the reaction is...

Embodiment 3

[0033] A kind of synthetic method of 2-amino-6-chloropurine, the concrete steps of this synthetic method are as follows:

[0034] S1: Add 280ml of 1,2-dichloroethane, 50ml of tetrahydrofuran and 25g of guanine into a dry reaction flask, add 35ml of phosphorus oxychloride dropwise at 25°C, and keep stirring for 2 hours after the addition is completed. The dropwise addition of phosphorus oxychloride is completed within 13 minutes;

[0035] S2: Then heat up to reflux reaction. After the reaction is completed, add 2g of developer to the reaction solution and drop it into 400ml of the mixed solution. React for 2h. Cool it to 13°C with ice water. After filtration, a solid reactant is obtained. The temperature of the temperature rise and reflux reaction is 50 ℃, the reaction time is 5h, the mixed solution is a mixture of tetraethylammonium chloride and acetonitrile anhydrous, wherein tetraethylammonium chloride: acetonitrile anhydrous=1:5;

[0036] S3: Mix the solid reactant with 15...

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Abstract

The invention discloses a synthesis method of 2-amino-6-chloropurine in the technical field of chemical synthesis. The synthesis method comprises the specific steps as follows: S1, 200-300 ml of 1,2-dichloroethane, 40-60 ml of tetrahydrofuran and 20-30 g of guanine are added to a dried reaction bottle, and 30-40 ml of phosphorous oxychloride is dropwise added; S2, 1-3 g of a developing agent is added to a reaction solution, 300-500 ml of a mixed solution is dropwise added, and a solid reactant is obtained after filtration; S3, the solid reactant and 100-200 ml of a 12% acetic acid solution aremixed to react at 70-80 DEG C for 1-2 h, and a wet product is obtained; S4, a crude 2-amino-6-chloropurine product is prepared; S5, filtration, washing and drying are performed and a refined 2-amino-6-chloropurine product is prepared. The method comprises simple and safe procedures, has high yield and low cost, is suitable for popularization and application, has low equipment requirements in thesynthesis process, produces few byproducts, has mild reaction conditions and cannot cause environmental pollution.

Description

technical field [0001] The invention discloses a synthesis method of 2-amino-6-chloropurine, and specifically belongs to the technical field of chemical synthesis. Background technique [0002] 2-Amino-6-chloropurine is an intermediate of antiviral agents famciclovir and panciclovir, and can also be used in the synthesis of anti-cancer, anti-inflammatory and blood pressure-lowering drugs. Its main synthetic routes are as follows: one is to use guanine to react with phosphorus pentasulfide, and then to react with chlorine to make it. This method has a strong smell, pollutes the environment, and thioguanine is unstable; Phosphorus is directly chlorinated and then hydrolyzed under the phase transfer catalyst tetramethylammonium chloride. This method has low product yield due to the low solubility of guanine, and a large amount of expensive phase transfer catalyst is used. For this reason, we propose A kind of synthetic method of 2-amino-6-chloropurine is put into use, to solve...

Claims

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Application Information

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IPC IPC(8): C07D473/40
CPCC07D473/40
Inventor 谢小坚梁荣强
Owner ZHONGSHAN DEGAOXING INTPROP CENT LLP
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