Collect. Czech. Chem. Commun. 1997, 62, 136-146

Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents

Michal Hocek, Milena Masojídková and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The title acyclic nucleotide analogues derived from 6-hetarylpurines were prepared by Pd(0)-catalysed cross-coupling reactions of 9-[2-(diethoxyphosphonylmethoxy)ethyl]-6-iodopurine (1) with hetarylorganometallics: (pyridin-2-yl)-, (imidazol-2-yl)- and (pyrrol-2-yl)zinc chlorides or (imidazol-5-yl)- stannanes, followed by deprotection in fair to good yields. The starting 6-iodopurine derivative 1 was prepared by iododeamination of the adenine derivative.

Keywords: Acyclic nucleoside phosphonates; Phosphonomethoxyethylpurine derivatives; PMEA; Organozinc reagents; Organotin reagents; Palladium; Antivirals.