A practical synthesis of 5-functionalized thieno[2, 3-d]pyrimidines. Issue 30 (22nd July 2015)

• Record Type: Journal Article
• Authors: Wilding, Birgit; Faschauner, Stefan; Klempier, Norbert
• Is Part Of: Tetrahedron letters. Volume 56:Issue 30(2015)
• Page Start: 4486
• Page End: 4489
• Publication Date: 2015-07-22
• Subjects: Thieno[2, 3-d]pyrimidine -- Thiophene -- Gewald reaction -- Functionalization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.104
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of 5-hydroxymethyl-, 5-acetoxymethyl-, 5-formyl- and 5-cyanothieno[2, 3- d ]pyrimidines, the (methyl)-5-carboxylate, and the respective amide functionality was accomplished by building up the functionalized molecule starting from appropriately substituted thiophene precursors. A similar strategy starting from the pyrimidine precursor and subsequent direct functionalization (formylation and cyanation) of the thieno[2, 3- d ]pyrimidine parent compound in position 5 was found to be less feasible.