Selective reduction of the 7-oxo group in pyrido[2,3d]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; Esther Couceiro

doi:10.3987/com-99-s129

Selective reduction of the 7-oxo group in pyrido[2,3d]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, Esther Couceiro

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1207-1214
Number of pages	8
Journal	Heterocycles
Volume	52
Issue number	3
DOIs	https://doi.org/10.3987/com-99-s129
Publication status	Published - 1 Mar 2000

Keywords

5,10-dideaza-5,6,7,8-tetrahydrofolic acid
Absolute-configuration
Asymmetric-synthesis
Organic-compounds
Purine synthesis
Folic-acid
Phase-i
Convergent
Diborane
Analogs

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title = "Selective reduction of the 7-oxo group in pyrido[2,3d]pyrimidine-4,7- diones: A new synthetic approach to 5,10-dideazatetrahydrofolic acid (DDATHF)",

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.",

keywords = "5,10-dideaza-5,6,7,8-tetrahydrofolic acid, Absolute-configuration, Asymmetric-synthesis, Organic-compounds, Purine synthesis, Folic-acid, Phase-i, Convergent, Diborane, Analogs",

author = "Borrell, {Jos{\'e} I.} and Jordi Teixid{\'o} and Matallana, {Josep Llu{\'i}s} and Blanca Mart{\'i}nez-Teipel and Esther Couceiro",

year = "2000",

month = mar,

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doi = "10.3987/com-99-s129",

language = "English",

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T1 - Selective reduction of the 7-oxo group in pyrido[2,3d]pyrimidine-4,7- diones

T2 - A new synthetic approach to 5,10-dideazatetrahydrofolic acid (DDATHF)

AU - Borrell, José I.

AU - Teixidó, Jordi

AU - Matallana, Josep Lluís

AU - Martínez-Teipel, Blanca

AU - Couceiro, Esther

PY - 2000/3/1

Y1 - 2000/3/1

N2 - 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.

AB - 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.

KW - 5,10-dideaza-5,6,7,8-tetrahydrofolic acid

KW - Absolute-configuration

KW - Asymmetric-synthesis

KW - Organic-compounds

KW - Purine synthesis

KW - Folic-acid

KW - Phase-i

KW - Convergent

KW - Diborane

KW - Analogs

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DO - 10.3987/com-99-s129

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JO - Heterocycles

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IS - 3

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Selective reduction of the 7-oxo group in pyrido[2,3d]pyrimidine-4,7- diones: A new synthetic approach to 5,10-dideazatetrahydrofolic acid (DDATHF)

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Keywords

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