NOVEL METHODOLOGY FOR THE PREPARATION OF 5-SUBSTITUTED TETRAHYDRO[2,3-D]DIPYRIMIDINES

Authors
WATSON SE TAYLOR EC PATEL H
Citation
Se. Watson et al., NOVEL METHODOLOGY FOR THE PREPARATION OF 5-SUBSTITUTED TETRAHYDRO[2,3-D]DIPYRIMIDINES, Synthetic communications, 28(10), 1998, pp. 1897-1905
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
28
Issue
10
Year of publication
1998
Pages
1897 - 1905
Database
ISI
SICI code
0039-7911(1998)28:10<1897:NMFTPO>2.0.ZU;2-Y
Abstract
A convenient, concise route for the preparation of tetrahydropyrido[2, 3-d]pyrimidines functionalized at the 5-position is presented starting from acyclic aldehydes. Key steps involve a high yielding Knoevenagel condensation, 1,4 conjugate addition with an allylcuprate and a pyrim idine annulation using guanidine hydrochloride. An improved synthesis of the starting aldehyde, ethyl 4-propalbenzoate is presented.