Scale-Up Synthesis of a TRPV1 Antagonist Featuring a Facile Thiazolo[5,4-d]pyrimidine Formation

An efficient and practical synthesis of a TRPV1 inhibitor bearing a thiazolo[5,4-d]pyrimidine core was developed. The initial synthesis was modified to facilitate acylation of 5-aminopyrimidine and subsequent thiazole formation. The synthesis features an efficient two-pot, five-step process for the...

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Bibliographic Details
Published in:Organic process research & development 2011-03, Vol.15 (2), p.382-388
Main Authors: Liu, Jing, Fitzgerald, Anne E, Lebsack, Alec D, Mani, Neelakandha S
Format: Article
Language:English
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Summary:An efficient and practical synthesis of a TRPV1 inhibitor bearing a thiazolo[5,4-d]pyrimidine core was developed. The initial synthesis was modified to facilitate acylation of 5-aminopyrimidine and subsequent thiazole formation. The synthesis features an efficient two-pot, five-step process for the construction of the thiazolo[5,4-d]pyrimidine ring. The new route is concise, chromatography-free, and amenable to large-scale preparation.
ISSN:1083-6160
1520-586X
DOI:10.1021/op1002984