Sodium Iodide → Thymine

Participants

Reaction Conditions

Reaction Steps

A solution of the 4'-α and 4'-β isomers of 3'-O-t-butyldimethylsilyl-4'-methanesulfonyloxymethylthymidine (88 mg, 0.18 mM) prepared, e.g., as described in Preparation 5, with NaI (270 mg, 1.8 mM) in 2,5-hexanedione (3 ml) was stirred at 130° C. for 2 hours, at 95° C. for 60 hours and at 130° C. for 24 hours. Solid material was filtered off and the solvent was removed by evaporation under reduced pressure. The residue was purified (twice) by flash chromatography on silica gel. The column was eluted with CH2Cl2 +4% CH3OH+0.05% acetic acid followed by CH2Cl2 +4% CH3OH. The two fractions with identical TLCs and were combined yielding a mixture of the 4'-α and 4'-β isomers of 3'-O--t-butyldimethylsilyl-4'-iodomethylthymidine (70 mg, 0.14 mM), as a light brownish material. MS(CI) 514(M+NH4)+.

Provenance & Evidence