64456-16-2Relevant academic research and scientific papers
3,9-Dialkylhypoxanthines
Itaya, Taisuke,Ogawa, Kazuo
, p. 1906 - 1913 (2007/10/02)
Reaction of 1-methyl-5-(methylamino)imidazole-4-carboxamide (6a) with a boiling mixture of ethyl orthoformate and acetic acid anhydride produced 3,9-dimethylhypoxanthine (7a) in 60percent yield and 1-methyl-5-(N-methylformamido)imidazole-4-carboxamide (5a) in 39percent yield.Compound 7a was transformed into 7a by treatment with NaH in 78percent yield.Compound 7a was alternatively prepared by cyclocondensation of 6a with diethoxymethane followed by oxidation with I2.The pyrimidine moiety of 7a has been shown to be reactive: 7a affords the 1,2-dihydro derivative 9 under reductive conditions and undergoes ring opening to 5a in aqueous NaOH. 3-Ethyl-9-methyl- (7b), 3-benzyl-9-methyl-(7c), 9-ethyl-3-methyl-(7d), and 3,9-dibenzylhypoxanthine (7e) were also prepared from the corresponding carboxamides 6b-e.Keywords-3,9-dialkylhypoxanthine; cyclocondensation; base-promoted cylization; 1,2-dihydrohypoxanthine; dihydropurine oxidation; purine reduction; pyrimidine ring cleavage
