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Synthesis 2007(1): 51-54  
DOI: 10.1055/s-2006-950380
PAPER
© Georg Thieme Verlag Stuttgart · New York

Two-Step Synthesis of (Z)-2-[2-Oxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ylidene]acetamide Derivatives from 2-Chloro-6-methylpyridine-3-carbonitrile

Kazuhiro Kobayashi*, Daisuke Iitsuka, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 10 August 2006
Publication Date:
12 December 2006 (online)

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Abstract

(Z)-2-[1-Aryl-7-methyl-2-oxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ylidene]acetamides were prepared using a two-step sequence. The first step was the addition of magnesium enol­ates of tertiary acetamides to 2-chloro-6-methylpyridine-3-carbo­nitrile to give vinylogous urea derivatives, (Z)-3-amino-3-(2-chloro-6-methylpyridin-3-yl)propenamides. In the second step, these were reacted with aryl isocyanates in the presence of sodium hydride to give the corresponding pyrido[2,3-d]pyrimidin-2(1H)-one derivatives.

Key words

isocyanate - magnesium amide - magnesium enolate - pyridinecarbonitrile - pyridopyrimidine