Synthesis of (E)-5-[2-(tri-n-butylstannyl)vinyl] substituted 2′-deoxyuridine derivatives for use in halogenation and radiohalogenation reactions

A facile synthesis is reported for 5-[2-(tri-n-butyl-stannyl)vinyl]-2'-deoxyuridine 1, starting from commercial 5-iodo-2'-deoxyuridine 2 via the stannylation reaction as the key step. The 3',5'-di-O-acetyl-N(3)-p-toluoyl-protected analog of 1, compound 9, was then prepared. Electrophilic fluorination of 9 with carrier-added [F-18]F-2 provided the desired (E) and (Z) fluorovinyl compounds 10, bur not as the major products. The E/Z ratio of 10 was 2:1. The main product of the reaction was the proton substituted compound 11.