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Synthesis method of hypoxanthine derivative under catalysis of nitric acid

A technology of nitric acid catalyzing hypoxanthine and a synthesis method, which is applied in the preparation of sugar derivatives, sugar derivatives, and sugar derivatives, etc., can solve the problems of corrosion equipment, harsh reaction conditions, poor substrate adaptability, etc.

Active Publication Date: 2021-10-08
XINXIANG UNIV
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  • Description
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Problems solved by technology

The disadvantage of this reaction system is that the strong alkali system corrodes the equipment, and the post-treatment requires a large amount of acid for neutralization, resulting in the by-product salt
[0005] 3. When 6-chloropurine derivatives are hydrolyzed in an acidic solvent, or in a strong acid environment, such as acetic acid, hydrochloric acid, etc. as the reaction solvent, there are also disadvantages such as harsh reaction conditions and poor substrate adaptability.

Method used

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  • Synthesis method of hypoxanthine derivative under catalysis of nitric acid
  • Synthesis method of hypoxanthine derivative under catalysis of nitric acid
  • Synthesis method of hypoxanthine derivative under catalysis of nitric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0028] In a reaction flask, add 6-chloropurine (0.154 g, 1 mmol) to acetonitrile (4 mL) and H 2 O (1mL), add 68% nitric acid (0.13μL, 0.02mmol), heat to 80℃, react for 2h, add saturated NaHCO 3 The solution was neutralized, the reaction solution was transferred to a concentrator, and concentrated under reduced pressure to obtain 0.125 g of hypoxanthine with a yield of 92%.

Embodiment 2

[0030] In a reaction flask, add 6-chloropurine (0.154 g, 1 mmol) to toluene (4 mL) and H 2 O (1mL), add 68% nitric acid (0.13μL, 0.02mmol), heat to 80℃, react for 2h, add saturated NaHCO 3 The solution was neutralized, the reaction solution was transferred to a concentrator, and concentrated under reduced pressure to obtain 0.116 g of hypoxanthine with a yield of 85%.

Embodiment 3

[0032] In a reaction flask, add 6-chloropurine (0.154 g, 1 mmol) to chloroform (4 mL) and H 2 O (1 mL), add 68% nitric acid (0.13 μL, 0.02 mmol), seal the reaction bottle, heat to 80 ° C for 4 h, add saturated NaHCO 3 The solution was neutralized, and the reaction solution was transferred to a concentration device, and concentrated under reduced pressure to obtain 0.103 g of hypoxanthine with a yield of 76%.

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Abstract

The invention discloses a synthesis method of a hypoxanthine derivative under catalysis of nitric acid, and belongs to the technical field of medicinal chemistry. The method comprises the following steps: mixing a 6-chloropurine derivative with a solvent, adding a catalytic amount of nitric acid, carrying out a heating reaction, neutralizing acid generated in the reaction, and removing the solvent under reduced pressure to obtain the hypoxanthine derivative. The hypoxanthine derivative obtained by adopting the method is low in cost, high in purity and good in substrate adaptability, various impurities in a traditional method are removed, separation and purification are convenient, and the reliability of the quality of the hypoxanthine derivative is indicated.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a method for synthesizing hypoxanthine derivatives catalyzed by nitric acid. Background technique [0002] Hypoxanthine derivatives have been widely used in chemotherapy, biochemistry and chemical synthesis. Such as inosine injection, clinically used for leukopenia or thrombocytopenia, various acute and chronic liver diseases, pulmonary heart disease, etc. Didanosine, also known as didanosine and didanosine, is an antiviral drug that is clinically used in combination with other antiviral drugs to treat type Ⅰ HIV infection. In addition, hypoxanthine derivatives can conveniently connect substituent groups to the 6-position of purine through carbonyl conversion reaction, so as to obtain drugs with higher physiological activity and better curative effect, which is an important way for the development of antiviral and antitumor drugs. At present, three types...

Claims

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Application Information

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IPC IPC(8): C07D473/18C07D473/30C07D473/40C07H1/00C07H19/16C07H19/173
CPCC07D473/18C07D473/40C07D473/30C07H19/16C07H19/173C07H1/00
Inventor 夏然陈磊山李峰杨政楠谢思琪孙爱丽
Owner XINXIANG UNIV
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