HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils.

Authors
Gambacorta, A Farah, ME Tofani, D
Citation
A. Gambacorta et al., HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils., TETRAHEDRON, 55(43), 1999, pp. 12615-12628
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
43
Year of publication
1999
Pages
12615 - 12628
Database
ISI
SICI code
0040-4020(19991022)55:43<12615:HDCIAO>2.0.ZU;2-O
Abstract
A qualitative hardness scale (N-1<N-3<O-4) has been found for the conjugate d bases of 2-methoxy-4(3H)-pyrimidinones 1-3 and applied to high yielding c hemoselective N-3 methylation, ethylation and benzylation reactions. Remova l of the 2-methoxy group followed by a second alkylation affords unsymmetri cally 1,3-disubstituted uracils. (C) 1999 Published by Elsevier Science Ltd . All rights reserved.