An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water

doi:10.6023/cjoc202104043

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3701-3709.DOI: 10.6023/cjoc202104043 Previous Articles Next Articles

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水介质中1H-吡唑并[3,4-d]嘧啶-4(5H)-酮的快捷高效合成

苏子琦^a, 张奇^a, 赵界强^a, 赵涛^a, 刘文艺^a, 王慧萍^b, 徐娟^b^,^*(), 李加荣^a^,^*()

a 北京理工大学化学与化工学院北京 102488
b 国家卫生健康委科学技术研究所北京 100081

收稿日期:2021-04-19 修回日期:2021-05-10 发布日期:2021-06-07
通讯作者: 徐娟, 李加荣
基金资助:
中国医学科学院医学与健康科技创新工程(2018-I2M-1-004); 中央级公益性科研院所基本科研业务费专项(2021GJZ05)

An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water

Ziqi Su^a, Qi Zhang^a, Jieqiang Zhao^a, Tao Zhao^a, Wenyi Liu^a, Huiping Wang^b, Juan Xu^b(), Jiarong Li^a()

a School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488
b National Research Institute for Family Planning, Beijing 100081

Received:2021-04-19 Revised:2021-05-10 Published:2021-06-07
Contact: Juan Xu, Jiarong Li
Supported by:
Chinese Academy of Medical Sciences Innovation Fund for Medical Sciences(2018-I2M-1-004); Non-profit Central Research Institute Fund of National Research Institute for Family Planing(2021GJZ05)

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Abstract

Abstract Pyrazolopyrimidinone compounds have many biological activities and been widely used due to the similar structure of purines in organisms. However, the traditional synthetic methods suffered from several drawbacks, such as acylation and cyclization. Herein, one pot cyclization of 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one was developed by one pot conversion of 5-amino-4-cyano-pyrazole and aromatic aldehydes in the presence of sodium hydroxide using water as media. The reaction was carried out under the conditions of easily available raw materials, simple operation, and showed good tolerance to various functional groups.

Key words: one pot conversion, pyrazolo[3,4-d]pyrimidin-4(5H)-one, sodium hydroxide, green solvent, water

Cite this article

Ziqi Su, Qi Zhang, Jieqiang Zhao, Tao Zhao, Wenyi Liu, Huiping Wang, Juan Xu, Jiarong Li. An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3701-3709.

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References 20

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Entry	Solvent	Cat. (equiv.)	Temp./℃	Yield^b/%
1	H₂O	NaOH (1.0)	Reflux	85
2	H₂O	NaOH (1.0)	80	70
3	H₂O	NaOH (1.0)	60	52
4	H₂O	NaOH (1.0)	20	—
5	H₂O	NaOH (0.5)	Reflux	63
6	H₂O	KOH (1.0)	Reflux	54
7	H₂O	—	Reflux	—
8	H₂O	ZnCl₂ (1.0)	Reflux	—
9	Toluene	ZnCl₂ (1.0)	80	—
10	DMSO	NaOH (1.0)	120	Trace
11	DMF	NaOH (1.0)	120	Trace
12	EtOH	NaOH (1.0)	Reflux	—
13	CH₃CN	NaOH (1.0)	Reflux	—
14	1,4-Dioxane	NaOH (1.0)	Reflux	20
15	Toluene	NaOH (1.0)	80	38

Entry	Solvent	Cat. (equiv.)	Temp./℃	Yield^b/%
1	H₂O	NaOH (1.0)	Reflux	85
2	H₂O	NaOH (1.0)	80	70
3	H₂O	NaOH (1.0)	60	52
4	H₂O	NaOH (1.0)	20	—
5	H₂O	NaOH (0.5)	Reflux	63
6	H₂O	KOH (1.0)	Reflux	54
7	H₂O	—	Reflux	—
8	H₂O	ZnCl₂ (1.0)	Reflux	—
9	Toluene	ZnCl₂ (1.0)	80	—
10	DMSO	NaOH (1.0)	120	Trace
11	DMF	NaOH (1.0)	120	Trace
12	EtOH	NaOH (1.0)	Reflux	—
13	CH₃CN	NaOH (1.0)	Reflux	—
14	1,4-Dioxane	NaOH (1.0)	Reflux	20
15	Toluene	NaOH (1.0)	80	38

水介质中1H-吡唑并[3,4-d]嘧啶-4(5H)-酮的快捷高效合成

An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water

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