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Preparation method of pyrazolo[3,4-d]pyrimidine amine compounds

A technology of pyrimidine amines and compounds, which is applied in the field of preparation of pyrazolo[3,4-d] pyrimidine amines, can solve the problem of little pesticide activity and achieve easy separation and purification, high product purity, good The effect of applying the foreground

Inactive Publication Date: 2015-09-23
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

We noticed that: from most of the literature reports, this kind of compound mainly shows pharmacological activity, and its pesticide activity is rarely reported

Method used

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  • Preparation method of pyrazolo[3,4-d]pyrimidine amine compounds
  • Preparation method of pyrazolo[3,4-d]pyrimidine amine compounds
  • Preparation method of pyrazolo[3,4-d]pyrimidine amine compounds

Examples

Experimental program
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Effect test

example 1

[0018]

[0019] Dissolve 3-methylthio-1-phenyl-4-cyano-5-triphenylphosphinoenylaminopyrazole (0.5 mmol) in 3 mL of dichloromethane, and add phenyl isocyanate ( 0.5-0.6mmol), let it stand for 12-24 hours, TLC tracking detection to complete reaction, then spin off the solvent, add 3mL methanol to the reaction system, and add one equivalent of sodium hydroxide, continue stirring at room temperature to 50°C 21h to the end of TLC detection. Finally, a large amount of white solid was precipitated, which was filtered by suction, and the reaction solution was concentrated and separated by column chromatography to obtain the corresponding 6-methoxy-3-methylthio-N,1-diphenyl-1H-pyrazolo[3 ,4-d]pyrimidin-4-amine 4a, white solid, yield

[0020] 89%. mp: 140-141 o C; IR (KBr, υ / cm -1 ): 3005, 2925, 2852, 1626, 1595, 1498, 1479, 1447, 1397, 1378, 1326, 1259, 1235, 752; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm), 2.75 (s, 3H), 4.06 (s, 3H), 7.15 (t, J = 7.2 Hz, 1H), 7.28 (t, J = 7.2 Hz...

example 2

[0022]

[0023] Dissolve 3-methylthio-1-phenyl-4-cyano-5-triphenylphosphinoenylaminopyrazole (0.5 mmol) in 3 mL of dichloromethane, and add 4-methylthiol at room temperature under nitrogen protection Phenyl isocyanate (0.5-0.6mmol), let it stand for 12-24 hours, TLC tracking detection to complete reaction, then spin off the solvent, add 3mL methanol to the reaction system, and add an equivalent of sodium hydroxide, at room temperature to 50 Stirring was continued for 21 h at °C until the end of TLC detection. Finally, a large amount of white solid was precipitated, which was filtered by suction, and the reaction solution was concentrated and separated by column chromatography to obtain the corresponding N-(4-methylphenyl)-6-methoxy-3-methylthio-1-phenyl -1H-pyrazolo[3,4-d]pyrimidin-4-amine 4b, white solid, yield 60%. mp 169-170 o C; IR (KBr, υ / cm -1 ): 3130, 2957, 1626, 1570, 1504, 1473, 1441, 1385, 1337, 1326, 1309, 1254, 862, 753; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm),...

example 3

[0025]

[0026] Dissolve 3-methylthio-1-phenyl-4-cyano-5-triphenylphosphinoenylaminopyrazole (0.5 mmol) in 3 mL of dichloromethane, and add 4-fluorobenzene at room temperature under nitrogen protection Base isocyanate (0.5-0.6mmol), let it stand for 12-24 hours, TLC tracking detection to complete reaction, then spin off the solvent, add 3mL methanol to the reaction system, and add one equivalent of sodium hydroxide, at room temperature to 50 ℃ Stirring was continued for 21 h until the end of TLC detection. Finally, a large amount of white solid was precipitated, and the reaction solution was concentrated by suction filtration and separated by column chromatography to obtain the corresponding N-(4-fluorophenyl)-6-methoxy-3-methylthio-1-phenyl- 1H-pyrazolo[3,4-d]pyrimidin-4-amine 4c, white solid, yield 75%. mp 177-179 o C; IR (KBr, υ / cm -1 ): 3130, 1629, 1591, 1505, 1468, 1410, 1384, 1336, 1307, 1255, 830, 751; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm), 2.74 (s, 3H), 4.03 (s, ...

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Abstract

A Preparation method of pyrazolo[3,4-d]pyrilamine compounds comprises the following steps: allowing phosphinimine prepared by pyrazole compounds with cyans and aminos at an ortho-position to react with various isocyanates by an aza-witting reaction under a mild condition in dichloromethane to obtain carbodiimide, then performing a cyclization reaction with alcohol in solvent alcohol with sodium hydroxide as an alkali so as to efficiently prepare the pyrazolo[3,4-d]pyrilamine compounds through a series process. The method of the invention is mild in reaction condition, wide in substrate application scope (R1=H or various electron-donating groups such as CH3, OCH3, OC2H5, and the like, or various electron-withdrawing groups such as 4-Cl, 4-F, and the like, wherein R2 is methanol or ethanol), less in side reaction, high in product purity, and convenient for separation and purification; the method is convenient for operation, low in cost, suitable for large-scale preparation, and has very good application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of pyrazolo[3,4-d]pyrimidine amine compounds. Background technique [0002] As a general structural skeleton, the pyrazolopyrimidinamine structure is one of the common heterocyclic structures, which widely exists in a variety of natural products and drug molecules with significant biological activities. Pharmacological studies have shown that these compounds are bactericidal and antifungal (Kreutzberger, A.; Burgwitz, K. Eur. J. Med. Chem. 1979, 14 ,539–41.), anti-tumor and cancer, anti-inflammatory, insecticide, plant regulator, etc. have very good effects. We noticed that from most of the literature reports, this kind of compounds mainly show pharmacological activity, and their pesticide activity is rarely reported. Therefore, we have carried out exploratory research on the synthesis method and pesticide activity of pyrazolopyrimidi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 王涛王文娟
Owner JIANGXI NORMAL UNIV
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