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Synthesis method of 2-acetamido-9-acetylpurine

A technology of acetyl purine and acetyl amino, which is applied in the field of synthesis of 2-acetylamino-9-acetyl purine, which can solve the problems of three wastes, easy removal of acetyl groups, and troublesome treatment.

Active Publication Date: 2021-08-06
SHANGHAI LINKCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are following problems in the synthetic method of current 2-acetylamino-9-acetyl purine, on the one hand, the reaction time is too long, as reported in patent WO 9315075, the reaction time needs 20-30h; on the other hand, the 9-position The acetyl group is easily removed during the post-treatment process, resulting in a monoacetylated product. In addition, in the traditional process, DMF, DMAc or acetic acid are used as solvents, and DMAP or p-toluenesulfonic acid is used as a catalyst to catalyze the reaction. However, the post-processing of these reagents is cumbersome and will produce more three wastes

Method used

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  • Synthesis method of 2-acetamido-9-acetylpurine
  • Synthesis method of 2-acetamido-9-acetylpurine

Examples

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Embodiment 1

[0023] The synthetic method of 2-acetylamino-9-acetylpurine

[0024] The preparation method of 2-acetylamino-9-acetylpurine provided in this example comprises the following steps:

[0025] Guanine (10g, 66.2mmol, 1eq), acetic anhydride (100g, 0.980mol) and tetrabutylammonium bromide (0.47g, 1.46mmol, 0.022eq) were added to the reaction vessel, the temperature was raised to 110°C, and the reaction was stirred 2 hours, then cooled to 25 ° C, filtered, the solid was separated from the filtrate, and the solid was dried at 50 ° C to obtain 15.2 g of 2-acetylamino-9-acetyl-6-hydroxypurine, the yield was 97.6%, the purity to 99.5%, the filtrate was concentrated under reduced pressure at 85°C, and the acetic acid could be recovered and used mechanically after separation.

[0026] figure 1 It is the hydrogen spectrum of 2-acetylamino-9-acetylpurine in Example 1 of the present invention.

[0027] like figure 1 As shown, the hydrogen spectrum data of 2-acetylamino-9-acetylpurine are ...

Embodiment 2

[0030] Screening of Catalysts in the Synthesis of 2-Acetylamino-9-Acetylpurine

[0031] In this example, the acetylation catalyst in the preparation method of 2-acetylamino-9-acetylpurine was screened, and the specific experimental operation was the same as in Example 1, the only difference being that the acylation catalyst used was different or the amount or reaction time was long The specific results are shown in Table 1.

[0032] Table 1 Catalyst Screening Table

[0033] serial number catalyst equivalent Response time yield purity 1 none - 2h Trace - 2 Tetrabutylammonium chloride 0.022eq 2h 96.8％ 99.5％ 3 Tetrabutylammonium bromide 0.05eq 2h 98.9％ 99.3％ 4 4-Methylaminopyridine 0.022eq 2h 38.1％ - 5 p-Toluenesulfonic acid 0.022eq 2h 22.3％ - 6 Tetramethylammonium chloride 0.022eq 2h 87.5％ 99.3％ 7 Dicyclohexylcarbodiimide 0.022eq 2h 40.5％ - 8 pyridine 0.022eq 2h 35.0％ - ...

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Abstract

The invention provides a synthetic method of 2-acetamido-9-acetylpurine, and belongs to the field of organic synthesis. The synthesis method of 2-acetamido-9-acetylpurine provided by the invention comprises the following steps: guanine, acetic anhydride and a catalyst are added into a reaction container, the temperature is raised to 100-120 DEG C, the reaction time is controlled to be 2-10 h, and separation and purification are performed to obtain 2-acetamido-9-acetylpurine, wherein the catalyst is quaternary ammonium salt. According to the invention, the quaternary ammonium salt is used as the reaction catalyst, so that the reaction time can be shortened to 2-10 hours, and the use of reagents which can cause high pollution can be avoided.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 2-acetylamino-9-acetylpurine. Background technique [0002] The derivatives obtained by introducing certain groups at positions 2, 6, 8, and 9 of guanine have important biomedical activities such as antiviral, anticancer, and blood pressure lowering. However, due to the existence of positions 2 and 9 in the purine molecule With active amino groups, in order not to destroy the molecular structure of purine when introducing groups, it is particularly important to protect the amino groups before introducing groups. [0003] There are following problems in the synthetic method of current 2-acetylamino-9-acetyl purine, on the one hand, the reaction time is too long, as reported in patent WO 9315075, the reaction time needs 20-30h; on the other hand, the 9-position The acetyl group is easily removed during the post-treatment process, resulting in a monoacetyl...

Claims

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Application Information

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IPC IPC(8): C07D473/18
CPCC07D473/18
Inventor 陆茜赵鑫刘海港
Owner SHANGHAI LINKCHEM TECH CO LTD
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