Chemoselective methylation of amides and heterocycles using chloromethyldimethylsilyl chloride

Authors
Bassindale, AR Parker, DJ Patel, P Taylor, PG
Citation
Ar. Bassindale et al., Chemoselective methylation of amides and heterocycles using chloromethyldimethylsilyl chloride, TETRAHEDR L, 41(25), 2000, pp. 4933-4936
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
25
Year of publication
2000
Pages
4933 - 4936
Database
ISI
SICI code
0040-4039(20000619)41:25<4933:CMOAAH>2.0.ZU;2-L
Abstract
The reaction of chloromethyldimethylsilyl chloride with an amide generates a pentacoordinate N-(amidomethyl)-halosilane that can be desilylated with c esium fluoride to give the N-methyl amide. This provides a selective method for the monoalkylation of amides in the presence of other, more nucleophil ic groups. (C) 2000 Elsevier Science Ltd. All rights reserved.