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Paper | Special issue | Vol 52, No. 3, 2000, pp.1207-1214
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S129
Selective Reduction of the 7-Oxo Group in Pyrido[2,3-d]pyrimidine-4,7-diones: A New Synthetic Approach to 5,10-Dideazatetrahydrofolic Acid (DDATHF)

José I. Borrell,* Jordi Teixidó, Josep Lluís Matallana, Blanca Martínez-Teipel, and Esther Couceiro

*Departament de Química Orgànica, Institut Quimic de Sarrià, Universitat Ramon Llull, E-08017 Barcelona, Spain

Abstract

A selective reduction of the carbonyl group at C7 with borane in THF is accomplished for 2,4-diamino-7-oxo and 2-amino-4,7-dioxo substituted pyridopyrimidines (7a-c) and (13a-c) respectively, the ester group remaining unaltered in both cases. The synthesis of 21c allows a new synthetic approach to 5,10-dideazatetrahydrofolic acid (DDATHF, 1) because it is a common intermediate in two procedures that afford the aforementioned antifolate.