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Synthetic method of high-purity high-yield theophylline

A synthesis method and a high-yield technology are applied in the field of high-purity and high-yield theophylline synthesis, can solve the problems of low purity of theophylline, low theophylline yield, complicated processes, etc., and achieve the safety and environmental protection of reagents and the preparation process. Simple, easy-to-operate preparation process

Inactive Publication Date: 2015-07-01
HEFEI PINGGUANG PHARMA
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the biological extraction method mainly uses tea leaves as raw materials, and theophylline is obtained through extraction, resin adsorption, purification and other steps, but the purity of theophylline is not high.
The chemical synthesis method is mostly prepared by the following two ways: one is to use 1,3-dimethyl-4-amino-5-formamidouracil and sodium hydroxide solution to react at 90-95°C to prepare tea The crude alkali product is obtained by hot water recrystallization and activated carbon decolorization to obtain the finished product, but the yield of theophylline is low; the second is to use ethyl cyanoacetate and dimethyl urea as raw materials, and undergo condensation, nitrosation, reduction, formylation, and cyclization Combined reaction to get crude product, and then recrystallization, but the process is complicated, and the yield of each step reaction is low

Method used

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preparation example Construction

[0030] The method for synthesizing theophylline with high purity and high yield provided by the present invention includes the following steps:

[0031] S1. Put sodium acetate trihydrate, 6-amino-1,3-dimethyluracil, and anhydrous acetic acid in the first reaction vessel, heat up to 124-127°C, keep for 28-31min, and cool down to 79-82 ℃, then add the mixed solution, reduce to room temperature, stir for 47-50h, after filtration, wash the filter cake with 98wt% glacial acetic acid, and then dry to obtain 6-amino-5-bromo-1,3-dimethyluracil , Where the mixed solution is made by mixing liquid bromine and anhydrous acetic acid;

[0032] S2. Add 6-amino-5-bromo-1,3-dimethyluracil and benzylamine into the second reaction vessel, raise the temperature to 98-100°C, keep the temperature for 1.9-2.2h, and keep the temperature up and down during the heat preservation process. Stop stirring, then lower to room temperature, add ice water until no solids continue to precipitate, wash the filter ca...

Embodiment 1

[0037] The method for synthesizing theophylline with high purity and high yield provided by the present invention includes the following steps:

[0038] S1. Put sodium acetate trihydrate, 6-amino-1,3-dimethyluracil, and anhydrous acetic acid in the first reaction vessel, heat up to 125°C, keep for 30min, cool down to 80°C, and then add the mixed solution , Cooled to room temperature, stirred for 48h, filtered, washed the filter cake with 98wt% glacial acetic acid, and then dried to obtain 6-amino-5-bromo-1,3-dimethyluracil, in which the mixed solution is composed of liquid bromine and Mixed with anhydrous acetic acid;

[0039] S2. Add 6-amino-5-bromo-1,3-dimethyluracil and benzylamine into the second reaction vessel, raise the temperature to 100℃, keep it for 2h, keep stirring during the heating process and the heat preservation process, and then reduce After reaching room temperature, add ice water until no solids continue to precipitate out, wash the filter cake with ice water a...

Embodiment 2

[0043] The method for synthesizing theophylline with high purity and high yield provided by the present invention includes the following steps:

[0044] S1. Molybdenum Put 1.4 parts of sodium acetate trihydrate, 2 parts of 6-amino-1,3-dimethyluracil, and anhydrous acetic acid in the first reaction vessel, raise the temperature to 124°C, keep the temperature for 31min, and cool it down to At 79°C, add the mixed solution, reduce to room temperature, stir for 50h, after filtration, wash the filter cake with 98wt% glacial acetic acid, and then dry to obtain 6-amino-5-bromo-1,3-dimethyluracil. The mixed solution is made by mixing 1 part of liquid bromine and 4.3 parts of anhydrous acetic acid;

[0045] S2. Add 6-amino-5-bromo-1,3-dimethyluracil and benzylamine into the second reaction vessel, increase the temperature to 98°C, keep the temperature for 2.2h, keep stirring during the heating process and the insulation process, and then After cooling down to room temperature, add ice water...

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Abstract

The invention discloses a synthetic method of high-purity high-yield theophylline. The synthetic method comprises the following steps: preparing 6-amino-5-bromo-1,3-dimethyl uracil by adopting sodium acetate trihydrate, 6-amino-1,3-dimethyl uracil, anhydrous acetic acid and liquid bromine; preparing 6-amino-5-benzylamino-1,3-dimethyl uracil by adopting 6-amino-5-bromo-1,3-dimethyl uracil and benzylamine; preparing 1,3-dimethyl-7-benzyl xanthene by adopting 6-amino-5-benzylamino-1,3-dimethyl uracil, p-toluene sulfonic acid, triethyl orthoformate and DMF (dimethyl formamide); and preparing theophylline from 1,3-dimethyl-7-benzyl xanthene, a palladium carbon catalyst and methanol in a hydrogen high-pressure environment. According to the synthetic method disclosed by the invention, the reaction starting material is simple and easy to obtain, the used reagents are safe and environment-friendly, the production cost is greatly reduced, and the preparation process is simple and easy to operate; and compared with the prior art, the reaction environment related to each step is small in pollution, and the yield and purity of obtained theophylline are greatly improved.

Description

Technical field [0001] The invention relates to the technical field of theophylline preparation, in particular to a method for synthesizing theophylline with high purity and high yield. Background technique [0002] Theophylline is 1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione, also known as dioxydimethylpurine, 1,3-dimethylxanthine, 1,3-Dimethylxanthine, etc., appearance is white crystal or crystalline powder, odorless, bitter taste, its molecular formula is C 7 H 8 N 4 O 2 , Molecular weight is 180.16, CAS number is 58-55-9, density is 1.62g / cm 3 , Melting point is 270-274℃, soluble in water, ethanol, chloroform, lye hydroxide, ammonia, dilute hydrochloric acid and dilute nitric acid at room temperature, slightly soluble in ether. It is a methylpurine drug that has the effects of strengthening the heart, diuresis, dilating coronary arteries, and stimulating the central meridian system. It can be used to treat bronchial asthma, emphysema, bronchitis, and cardiac dyspnea. Its str...

Claims

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Application Information

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IPC IPC(8): C07D473/08
CPCC07D473/08
Inventor 王康林张成栋
Owner HEFEI PINGGUANG PHARMA
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