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Synfacts 2007(6): 0655-0655  
DOI: 10.1055/s-2007-968523
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a 2,6,8,9-Tetrasubstituted Purine Library

Contributor(s): Yasuhiro Uozumi, Yohei Oe
L. G. J. Hammarström, D. B. Smith*, F. X. Talamás
Roche Palo Alto LLC, USA
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

ArgoGel-MB-CHO resin 1 was treated with amines 2 in the presence of Na(OAc)3BH to give the resin-bound amines 3. Reaction of 3 with 4,6-dichloro-2-(methylthio)-5-nitropyrimidine 4, followed by treatment of the resulting 5 with amines 6 afforded 7. After the oxone-mediated oxidation of the methylthio group to the sulfone 8, the substitution with amines 9 was carried out at room temperature to give 10. Reduction of the nitro group by CrCl2 gave 11, which underwent cyclization with orthoesters 12 to give the resin-bound purines 13. Cleavage of the polymer support provided 2,6,8,9-tetrasubstituted purines 14 in 18-98% purity.