Synthesis of pyrrolo[2,3-d]pyrimidines via cyclocondensation of beta-alkoxy- and beta-amino-alpha-bromoaldehydes

Authors
Barnett, CJ Grubb, LM
Citation
Cj. Barnett et Lm. Grubb, Synthesis of pyrrolo[2,3-d]pyrimidines via cyclocondensation of beta-alkoxy- and beta-amino-alpha-bromoaldehydes, TETRAHEDR L, 41(50), 2000, pp. 9741-9745
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
50
Year of publication
2000
Pages
9741 - 9745
Database
ISI
SICI code
0040-4039(200012)41:50<9741:SOPVCO>2.0.ZU;2-N
Abstract
A series of beta -alkoxy- and beta -amino-alpha -bromoaldehydes was synthes ized. The cyclocondensation of these intermediates with 2,4-diamino-6-hydro xypyrimidine yielded a series of pyrrolo[2,3-d]pyrimidines containing heter oatoms in the side chain. Choice of protecting group proved critical to the success of the bromination and cyclocondensation reactions. A number of ox ygen and nitrogen protecting groups were examined and the results are descr ibed herein. (C) 2000 Elsevier Science Ltd. All rights reserved.