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)

Authors
Borrell, JI Teixido, J Matallana, JL Martinez-Teipel, B Couceiro, E
Citation
Ji. Borrell et al., 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), HETEROCYCLE, 52(3), 2000, pp. 1207
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
3
Year of publication
2000
Database
ISI
SICI code
0385-5414(20000301)52:3<1207:SROT7G>2.0.ZU;2-H
Abstract
A selective reduction of the carbonyl group at C7 with borane in THF is acc omplished for 2,4-diamino-7-oxo and 2-amino-4,7-dioxo substituted pyridopyr imidines (7a-c) and (13a-c) respectively, the ester group remaining unalter ed in both cases. The synthesis of 21c allows a new synthetic approach to 5 ,10-dideazatetrahydrofolic acid (DDATHF, 1) because it is a common intermed iate in two procedures that afford the aforementioned antifolate.