Abstract: A one-step synthesis of regioisomeric N-and O-benzylated 8-bromoguanines 4, 5, 9, 10 via N2-acetyl-8-bromoguanine (2) is described. The possibility to prepare 8-oxo-and 8- chloroguanine derivatives 3, 11, 12 from the same compound 2 is demonstrated. 1H and 13C NMR spectra are used to locate the sites of aralkylation. Key words: N2-acetyl-8- bromoguanine, benzylation, regioisomers