851370-52-0Relevant articles and documents
2-(Benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors
Taddei, David,Slawin, Alexandra M. Z.,Woollins, J. Derek
, p. 939 - 947 (2007/10/03)
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.
