Synthesis of a 5-alkoxypyrido [3, 4-d] pyrimidin-4 (3H)-one derivative via directed ortho-metallation of a pyridine analogue

AP Dishington, PD Johnson, JG Kettle

Index: Dishington, Allan P.; Johnson, Paul D.; Kettle, Jason G. Tetrahedron Letters, 2004 , vol. 45, # 19 p. 3733 - 3735

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Citation Number: 16

Abstract

As part of an ongoing research programme, we sought to investigate the structure–activity relationships around a series of 5-alkoxyquinazolin-4(3H)-one derivatives as exemplified by 1. These compounds were readily accessible to us via nucleophilic aromatic substitution (S N Ar) of commercially available 5-fluoroquinazolin-4(3H)-one, with alkoxide nucleophiles formed in situ by sodium hydride deprotonation of the appropriate alcohols. As part of these studies we became interested in the effects of ...