Abstract

Abstract The synthesis of the pyrido[4,3-d]pyrimidine congeners (7 and 8) of inosine and adenosine from the known precursor 3-dimethylamino-2-(2,3-0-isopropylidene-5–0-trityl-D-ribofuranosyl)acrylonitrile (10) is described. The synthetic sequence involves a modified Thorpe-Ziegler annulation to a 4-amino-3-cyanotetrahydropyridine derivative (22) followed by aromatization to an α, β mixture of the desired 5-ribosyl-4-amino-3-cyanopyridine intermediates (25 and 26). Further annulation to the pyrido[4,3-d]pyrimidine ring system and simultaneous detritylation and deisopropylidenation completes the synthesis.

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