Analogs of purine nucleosides. 3. Alkoxyalkylation of hypoxanthine by the silyl method

The reaction of bis(trimethylsilyl)hypoxanthine with methyl trichloromethyl ether has been investigated. 1-Methoxymethyl-, 7-methoxymethyl-, and 9-methoxymethyl-hypoxanthine, as well as 1,7-, 1,9-, and 3,7-bismethoxymethylhypoxanthine, have been isolated from the reaction mixture. The structures of the isomers have been established on the basis of an analysis of their UV, IR, 1H NMR, 13C NMR, and 15N NMR spectra. The influence of the conditions under which the reaction is carried out on the yield of the alkylation products and the isomeric composition of the reaction mixture has been studied.