Purines, pyrimidines, and imidazoles. Part 56. Some aminoimidazole-carboxamidines and derived adenines

Abstract

5-Amino-4-cyano-1-cyclohexylimidazole, prepared from aminomalononitrile, triethyl orthoformate, and cyclohexylamine with methanolic hydrogen chloride, produced methyl 5-amino-1-cyclohexylimidazole-4-carboximidate, which with ammonia gave 5-amino-1-cyclohexylimidazole-4-carboxamidine, formylation of which gave 9-cyclohexyl-N⁶-formyladenine, which was also prepared by formylation of 9-cyclohexyladenine. 9-(2,3-Dihydroxypropyl)-N⁶-formyladenine was produced in a similar series of reactions and the reaction of 5-aminoimidazole-4-carboxamidine with formic acetic anhydride has also been shown to produce not, as previously thought, the formylamidine, but N⁶-formyladenine which could also be obtained by formylation of adenine, whereas adenosine was not N-formylated under the same conditions.