Trimethylsilyl triflate → HCID 16735277, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,6-dichloropurine (2.29 g, 22.12 mmol) and ammonium sulfate (438 mg, 3.32 mmol) in hexamethyldisilazane (HMDS, 50 ml) was fluxed overnight under inert, dry conditions. The resulting reaction mixture was concentrated in a vacuum and the solid mixture thus formed was re-dissolved in cold 1,2-dichloroethene (20 ml). To this solution were dropwise added a solution of (3aR,4R,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl acetate (1.41 g, 11.06 mmol), obtained in Preparation Example 1, in 1,2-dichloroethane (20 ml), and then trimethylsilyl trifluoromethanesulfonate (TMSOTf, 4.0 ml, 22.12 mmol). The resulting solution was stirred at 0° C. for 30 min and then at room temperature for 1 hr, and heated at 80° C. for 2 hrs with stirring. The reaction mixture was cooled, diluted in dichloromethane and washed with a saturated aqueous sodium hydrogen carbonate (NaHCO3) solution. The organic solvent was dried over anhydrous magnesium sulfate (MgSO4) and concentrated in a vacuum to give a residue in the form of a yellow syrup. The residue was purified through silica gel column chromatography using a mixture of dichloromethane:methanol (50:1, v/v) as an elution solvent to afford the object compound in the form of a foam (3.03 g, 79%).

Provenance & Evidence