Tributylstannane → HCID 67687191, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 ml round-bottom flask equipped with condenser, nitrogen inlet, and thermometer was added 5'-benzoyl-3'-methanesulfonyl-2'-bromo-thymidine (5) (3.0 g, 5.96 mmol) and 30 ml of the specified solvent (see the table below). Bu3SnH (3.0 ml, 11.15 mmol; 1.9 equiv) was then added. The reaction mixture was heated to reflux or to the temperature specified in the table, to give a clear, homogeneous solution. The reaction mixture was then cooled slightly and 300 mg AIBN was added. The mixture was heated to reflux or the temperature specified in table for 45 minutes at which time the reaction was complete by HPLC (or for a period of time as specified in the table). The mixture was then cooled to 25° C. and concentrated to give a residue. The residue was purified by silica gel column chromatography (Kiesgel 60, 230-400 mesh silica gel, 2.5×23 cm column, 3/1 EtOAc/hexane as eluent) or by methylene chloride trituration to afford 5'-benzoyl-3'-methanesulfonylthymidine (6). These results were summarized in the table.

Provenance & Evidence