Synthesis of N2‐Substituted Deoxyguanosine Nucleosides from 2‐Fluoro‐6‐ O ‐(Trimethylsilylethyl)‐2′‐Deoxyinosine

Syntheses of N2‐substituted nucleosides have been studied for many years, primarily with ribonucleosides. However, the primary route to these compounds requires acidic conditions that are too vigorous for the acid‐labile deoxyribonucleosides. The current strategy takes advantage of methods for low‐temperature, nonaqueous diazotization of ribosides in organic solvents using t‐butyl nitrate as the diazotizing agent and HF/pyridine as the fluoride source for the preaparation of a 2‐fluoro‐2?‐deoxyinosine derivative that can be used to synthesize N2‐substituted deoxyguanosine.