Palladium-catalyzed allylic coupling of 1,2,3-triazolo[4,5-d]pyrimidines (8-azapurines)

Michael J. Konkel, Robert Vince

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The palladium-catalyzed coupling of the sodium salt of 7-amino-1,2,3-triazolo[4,5-d]pyrimidine (8-azaadenine, 1) with allylic phosphates or carbonates resulted in mixtures of 2- and 3-substituted 1,2,3-triazolopyrimidines, which were separated by chromatography. 1-Substituted triazolopyrimidines were not isolated from these reactions. Regioselectivity (and stereoselectivity) was also observed for substitution of the allylic moiety when more than one isomer is possible from the reaction. The use of 5-amino-1,2,3-triazolo[4,5-d]pyrimidin-7-ones (8-azaguanine, 2), instead of 8-azaadenine, also resulted in mixtures. Alternate syntheses of the 3-allyl-1,2,3-triazolo[4,5-d]-pyrimidines confirmed the structures of these compounds.

Original languageEnglish (US)
Pages (from-to)6199-6204
Number of pages6
JournalJournal of Organic Chemistry
Issue number18
StatePublished - Sep 6 1996


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