jo0517702_si_002.pdf (1.82 MB)
Single-Step Syntheses of 2-Amino-7-chlorothiazolo[5,4-d]pyrimidines: Intermediates for Bivalent Thiazolopyrimidines
journal contribution
posted on 2005-11-25, 00:00 authored by Jian Liu, Raymond J. Patch, Carsten Schubert, Mark R. PlayerA single-step process for the preparation of 2-amino-7-chlorothiazolo[5,4-d]pyrimidines, 2, was achieved by the
reaction of the commercially available 4,6-dichloro-5-aminopyrimidine 1 with isothiocyanates. This mild reaction
accommodates a variety of functionalized isothiocyanates
and proceeds in good to excellent yields. The utility of such
intermediates is exemplified by subsequent reaction with
alkyl or arylamine nucleophiles to afford novel, differentially
functionalized 2,7-diaminothiazolo[5,4-d]pyrimidines, 3.