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Synthesis of 6-substituted 1-alkoxy-5-alkyluracils

✍ Scribed by Dae-Kee Kim; Young-Woo Kim; Key H. Kim

Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 346 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340148

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✦ Synopsis

Abstract

Synthesis of 6‐substituted 1‐alkoxy‐5‐alkyluracils 2a‐c have been achieved from readily accessible 2‐alkyl‐3,3‐di(methylthio)acryloyl chlorides 4a,b in high overall yields. Treatment of 4a,b with silver cyanate followed by reaction of the resulting isocyanates 5a,b with an appropriate alkoxyamine afforded N‐alkoxy‐N′‐[2‐alkyl‐3,3‐di(methylthio)acryloyl]ureas 6a,b in 85–88% yields. Cyclization of 6a,b in acetic acid containing methanesulfonic acid followed by oxidation with 3‐chloroperoxybenzoic acid gave high yields of 1‐alkoxy‐5‐alkyl‐6‐(methylsulfonyl)uracils 9a,b. Nucleophillic addition‐elimination reaction of 9a,b with sodium azide, phenylthiol, or phenylselenol produced 6‐azido‐1‐butoxythymine (2a, 98%), 5‐ethyl‐1‐(2‐phenoxyethoxy)‐6‐(phenylthio)uracil (2b, 95%), or 5‐ethyl‐1‐(2‐phenoxyethoxy)‐6‐(phenylselenenyl)uracil (2c, 91%).

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