Collect. Czech. Chem. Commun. 1998, 63, 407-415

Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones

Ondrej Šimo, Alfonz Rybár and Juraj Alföldi

Institute of Chemistry, Slovak Academy of Sciences, SK-842 38 Bratislava, Slovak Republic


New 4-alkyl- or 4-phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones 1 were obtained by intramolecular alkylation of 8-alkyl- or 8-phenyl-9-(2-mesyloxyethyl)-1-methyl-9H-purine-2,6(1H,3H)-diones 5. The necessary compounds 5 were prepared from 6-[(2-hydroxyethyl)- amino]-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione (2), which was hydrogenated to 5-amino-6-[(2-hydroxyethyl)amino]-3-methyl derivative 3; consecutive reactions of the latter with an orthocarboxylate and mesyl chloride afforded 8-alkyl- or 8-phenyl-9-(2-hydroxyethyl)-1-methyl-9H-purine- 2,6(1H,3H)-diones 4 and compounds 5, respectively.

Keywords: Imidazo[1,2,3-cd]purines; 3,9-Annelated purines; Xanthine derivatives; Acyclic nucleoside analogues.