Nucleic acid related compounds, part 123.: SNAr iodination of 6-chloropurine nucleosides:: Aromatic Finkelstein reactions at temperatures below -40°C

Mesitoyl or toluoyl esters of inosine and 2'-deoxyinosine were deoxychlorinated at C6 to give the crystalline 6-chloropurine nucleoside derivatives, which underwent quantitative conversion to the 6-iodo analogues with Nal/TFA/butanone at -50 to -40 degreesC. The 6-iodo compounds were efficient substrates for SNAr, Sonogashira, and Suzuki-Miyaura reactions, in contrast with the 6-chloro analogues, and gave good to high yields of C-N and C-C coupled products.