Synthesis of 4-(trihalomethyl)dipyrimidin-2-ylamines from β-alkoxy-α,β-unsaturated trihalomethyl ketones

✍ Scribed by Nilo Zanatta; Elizandra C. S. Lopes; Leonardo Fantinel; Helio G. Bonacorso; Marcos A. P. Martins

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 43 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390514

✦ Synopsis

Abstract

The synthesis of a novel series of twelve 4‐(trihalomethyl)dipyrimidin‐2‐ylamines, from the cyclo‐condensation reaction of 4‐(trichloromethyl)‐2‐guanidinopyrimidine, with β‐alkoxyvinyl trihalomethyl ketones, of general formula: X~3~C‐C(O)‐C(R^2^)=C(R^1^)‐OR, where: X = F, Cl; R = Me, Et, ‐(CH~2~)~2~‐, ‐(CH~2~)~3~‐; R^1^ = H, Me; R^2^ = H, Me, ‐(CH~2~)~2~‐, ‐(CH~2~)~3~‐, is reported. The reactions were carried out in acetonitrile under reflux for 16 hours, leading to the dipyrimidin‐2‐ylamines in 65‐90% yield. Depending on the substituents of the vinyl ketone, tetrahydropyrimidines or aromatic pyrimidine rings were obtained from the cyclization reaction. When X = Cl, elimination of the trichloromethyl group was observed during the cyclization step. The structure of 4‐(trihalomethyl)dipyrimidin‐2‐ylamines was studied in detail by ^1^H‐, ^13^C‐ and 2D‐nmr spectroscopy.