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Synthesis of herbicidal 3-substituted-4(3H)-pyrimidinones under high pressure

✍ Scribed by Artur Jezewski; Janusz Jurczak; Zev Lidert; Colin M. Tice

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
54 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of an N‐monosubstituted amidine with a β‐ketoester to afford a pyrimidinone is sluggish at best under normal conditions. We now report that this reaction can be effected in moderate yield under high pressure. Thus, 2,6‐dichloro‐4‐pyridyl‐(N‐prop‐2‐ynyl)carboxamidine (4b) was reacted with three α‐substituted‐β‐ketoesters (2b‐d) at 10–16 kbar to afford herbicidal 2‐(2,6‐dichloro‐4‐pyridyl)‐3‐(prop‐2‐ynyl)‐4(3__H__)‐pyrimidinones 5b and 5c in 15 ‐ 43% yield. This result expands the scope of reactions promoted by application of high pressure.

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