High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

Sally Ann Poulsen; David J. Young; Ronald J. Quinn

doi:10.1016/S0960-894X(00)00620-X

High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

Sally Ann Poulsen, David J. Young, Ronald J. Quinn

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A₁ receptor than the R enantiomer 12.

Original language	English
Pages (from-to)	191-193
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	2
DOIs	https://doi.org/10.1016/S0960-894X(00)00620-X
Publication status	Published - Jan 2001
Externally published	Yes

Access to Document

10.1016/S0960-894X(00)00620-X

Cite this

@article{b30a3c29a06148e9af05cea8acab4fae,

title = "High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines",

abstract = "The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12.",

author = "Poulsen, {Sally Ann} and Young, {David J.} and Quinn, {Ronald J.}",

year = "2001",

month = jan,

doi = "10.1016/S0960-894X(00)00620-X",

language = "English",

volume = "11",

pages = "191--193",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "2",

}

TY - JOUR

T1 - High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

AU - Poulsen, Sally Ann

AU - Young, David J.

AU - Quinn, Ronald J.

PY - 2001/1

Y1 - 2001/1

N2 - The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12.

AB - The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12.

UR - http://www.scopus.com/inward/record.url?scp=0035931570&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(00)00620-X

DO - 10.1016/S0960-894X(00)00620-X

M3 - Article

C2 - 11206456

AN - SCOPUS:0035931570

VL - 11

SP - 191

EP - 193

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 2

ER -

High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

Abstract

Access to Document

Other files and links

Fingerprint

Cite this