Collect. Czech. Chem. Commun. 1999, 64, 685-695

Purine Nucleoside Analogues. 11. An Alternative Synthesis of N- and O-Alkyl Derivatives of 9- and 7-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine

Marina Madrea,*, Natella Panchenkoa, Alexander Golbraikha, Regina Zhuka, Upendra K. Panditb, Jan Geenevasenb and Gerrit-Jan Koomenb

a Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
b Laboratory of Organic Chemistry, University of Amsterdam, 1018 WS Amsterdam, The Netherlands


Alkylations of 9- and 7-[(2-acetoxyethoxy)methyl]-N2-acetylguanine with alkyl halogenides in the presence of base have been investigated affording a new route to the preparation of 1,N2-dimethyl- as well as O6-benzyl-9(7)-alkoxyalkylguanines. 1H NMR spectra revealed that the 1,N2-dimethyl derivatives exist as mixtures of two conformers at room temperature due to the restricted rotation about the C2-N2 bond. These findings agreed with conformational calculations.

Keywords: Purines; Nucleosides; Acyclic nucleoside analogues; Acyclovir; Alkylation.