One-Pot stereoselective synthesis of trans-4,5-dialkoxy-1,3-bis (2-pyrimidinyl)imidazolidines through a three-component reaction

✍ Scribed by Mehdi Ghandi; Farshid Salimi; Abolfazl Olyaei

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 238 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430342

✦ Synopsis

Abstract

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Stoichiometric reaction of 2‐aminopyrimidine with formaldehyde in the presence of formic acid catalyst in water gave N,N′‐bis(2‐pyrimidinyl)methanediamine (5). Subsequent cyclocondensation of 5 with glyoxal in alcohol (MeOH, EtOH, PrOH and i‐PrOH) under reflux conditions led to the formation of the corresponding 4,5‐dialkoxy‐1,3‐bis(2‐pyrimidinyl)imidazolidines (6a‐d). 4,5‐Dihydroxy‐1,3‐bis(2‐pyrimidinyl) imidazolidine (6e) was obtained when the reaction was carried out in acetonitrile. Based on ^1^H NMR analysis, it was found that the trans‐dialkoxyimidazolidines (6) were selectively obtained in these cyclocondensation reactions.