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Synthetic method for adenine

A synthesis method and adenine technology are applied in the field of chemical synthesis routes of adenine, which can solve the problems of long synthesis routes, high raw material prices, unsuitability for large-scale production and the like, and achieve the effect of easy operation.

Active Publication Date: 2014-04-09
ZHEJIANG CHENGYI PAHRMACEUTICAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method not only has a long synthetic route, but also has high raw material prices, serious pollution, low total yield, and is not suitable for large-scale production.

Method used

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  • Synthetic method for adenine
  • Synthetic method for adenine
  • Synthetic method for adenine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Step 1: Synthesis of 4,6-diamino-2-mercaptopyrimidine

[0086] Add 75 g of sodium ethoxide, 80 g of thiourea and 66 g of malononitrile into a 1000 mL three-necked flask, add 500 mL of absolute ethanol, stir, and heat to boiling. Reflux for 2h. Stop heating. Filter after cooling to obtain 4,6-diamino-2-mercaptopyrimidine filter cake, which is directly put into the next reaction. The yield is 75% based on malononitrile.

[0087] Step 2: Synthesis of 4,6-diamino-2-sulfinylpyrimidine

[0088] Dissolve the 4,6-diamino-2-mercaptopyrimidine filter cake obtained in step 1 in 1.0L 1mol / L sodium hydroxide solution, cool to -10°C, and add 150mL 30%H dropwise 2 O 2 The solution was stirred for 20 minutes, and then the pH of the reaction solution was adjusted to 4.5-5.0 with acetic acid. Filter to obtain 4,6-diamino-2-sulfinyl pyrimidine filter cake, which is directly used in the next reaction. The yield is calculated as 100%.

[0089] Step 3: Synthesis of 4,6-diaminopyrimidine

[0090]...

Embodiment 2

[0098] Step 1: The amount of ethanol was changed to 0.8L, and the other conditions were the same as step 1 in Example 1.

[0099] The synthesis reaction temperature of 4,6-diamino-2-sulfinopyrimidine was changed to -5°C, and other conditions were the same as step 2 of Example 1.

[0100] Step 3: The synthesis of 4,6-diaminopyrimidine is the same as step 3 in Example 1.

[0101] The synthesis of 4,6-diamino-5-nitrosopyrimidine is the same as step 4 in Example 1.

[0102] Step 5: Synthesis of 4,5,6-triaminopyrimidine

[0103] The moist 4,6-diamino-5-nitrosopyrimidine obtained in step 4 was added to an autoclave containing 400 mL of ethanol, 8 g of Raney nickel was added, hydrogen gas was added, stirred at room temperature for 10.0 h, filtered, and the filtrate was evaporated Remove methanol. The obtained 4,5,6-triaminopyrimidine was directly used in the next reaction. The yield is based on 95%.

[0104] Step 6: The cyclization agent used was changed to 0.8L formic acid, and other condit...

Embodiment 3

[0106] The synthesis of 4,6-diamino-2-mercaptopyrimidine was the same as step 1 in Example 1.

[0107] Step 2: The concentration of sodium hydroxide is changed to 1.2 mol / L, and other conditions are the same as step 2 of Example 1.

[0108] The synthesis of 4,6-diaminopyrimidine is the same as step 3 in Example 1.

[0109] Step 4: The input amount of sodium nitrite is changed to 164g, and the other conditions are the same as step 4 of embodiment 1.

[0110] Step 5: Synthesis of 4,5,6-triaminopyrimidine.

[0111] The moist 4,6-diamino-5-nitrosopyrimidine obtained in step 4 was added to an autoclave containing 400 mL of methanol, 4 g of 5% palladium carbon was added, hydrogen gas was added, and the mixture was stirred at room temperature for 8.0 h. After the reaction was completed, it was filtered, and the filtrate was evaporated to remove methanol. The obtained 4,5,6-triaminopyrimidine was directly used in the next reaction. The yield is based on 95%.

[0112] Step 6: The cyclization a...

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Abstract

The invention discloses a synthetic method for adenine. Malononitrile and thiourea are employed as raw materials. The raw materials are subjected to a cyclization reaction under action of sodium alkoxide, and 4,6-diamino-2-sulfydryl pyrimidine. Then through three reaction routes, adenine is obtained. Though the method has many reaction steps, no refining or drying are needed for the product of each reaction step, the product can be used in the next reaction step, and the operation is simple. The raw materials are easily available, the prices are relatively low, the reaction conditions are mild, the operation is simple, the reaction steps are decreased, the reaction time is shortened, the overall reaction yield is high, and the synthetic method is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis route of adenine. (2) Background technology [0002] Adenine, called 6-aminopurine in Chinese, is an important pharmaceutical raw material and intermediate. Mainly used in the production of anti-hepatitis B drug adefovir dipivoxil and anti-AIDS drug tenofovir dipivoxil, vitamin B 4 , Adenosine and plant growth hormone 6-benzyl adenine. [0003] At present, adenine is mainly prepared by the following methods: [0004] 1. Using hypoxanthine as raw material [0005] The Soviet patent USSR 1089093 reported a process route for preparing adenine by chlorination and ammoniation using hypoxanthine as a raw material. Hypoxanthine is obtained by cleavage of inosine, which is produced by biological fermentation. This route is restricted and restricted by the source of hypoxanthine. CN 102321086A reports that acetyl hypoxanthine is used as a raw material to obtain adenine through chlorination and ammoniating. There are ...

Claims

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Application Information

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IPC IPC(8): C07D473/34
CPCC07D473/34
Inventor 李永曙王云龙
Owner ZHEJIANG CHENGYI PAHRMACEUTICAL
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