2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors

doi:10.1002/EJOC.200400748

Paper

2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors

Published Mar 1, 2005 · D. Taddei, A. Slawin, J. Woollins

European Journal of Organic Chemistry

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Abstract

The synthetic potential of a novel precursor of 2,6-diaminopurine CDK inhibitors, 2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, is described. The Traube purine synthesis was chosen to prepare the required 2-(benzylsulfanyl)hypoxanthine intermediate. Attempts to prepare its purin-6-yl methanesulfonic ester analogue failed. Conversion to the 6-chloropurine derivative enabled the introduction of arylamines in the presence of catalytic amounts of acid. Further chemical variety was introduced on the purine through a regioselective Mitsunobu N-9 alkylation. Oxidative cleavage of the 2-(benzylsulfanyl) leaving group with an aliphatic amine was implemented as previously reported. Purvalanol A, a potent CDK inhibitor, was synthesised using this methodology. The template and intermediates were fully characterised by modern spectroscopic techniques and single-crystal X-ray diffraction. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

Study Snapshot

The novel precursor 2-(benzylsulfanyl)-6-chloro-9-isopropylpurine shows potential for the synthesis of diaminopurine cyclin dependent kinase inhibitors, such as Purvalanol A.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors

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Citations

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