Journal
JOURNAL OF COMBINATORIAL CHEMISTRY
Volume 11, Issue 3, Pages 495-499Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cc900023s
Keywords
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Funding
- Center for Biological Modulators of the 21st Century Frontier RD Program [CBM32-B1000-01-00-00]
- R&D Program, Ministry of Education, Science and Technology, Korea. [2009-05681]
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An expedient, traceless, solid-phase synthesis of 2,4,6-trisubstituted thiazolo[4,5-d]pyrimidine-5,7-dione derivatives has been developed. The solid-phase synthetic route utilizes urea formation by a microwave irradiation promoted reaction of a thiazole amino ester resin with an isocyanate. The resulting urea resin is converted to a thiazolopyrimidinedione resin, containing two diversity elements at N-4 and N-6 by using, a one-pot cyclization/N-alkylation process. After oxidation to form a sulfone, nucleophilic C-2 substitution with amines, the third diversity element, gives the target 2,4,6-trisubstituted thiazolo[4,5-d]pyrimide-5,7-dione derivatives. This highly efficient solid-phase synthetic sequence enables the incorporation of three points of diversity into the preparation of the thiazolo[4,5-d]pyrimidine-5,7-dione ring system.
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