Methyl iodide → HCID 67164342, compound

Participants

Reaction Steps

To a solution of (2R,3S,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-[6-(2-phenylethyl)-9H-purin-9-yl]tetrahydrofuran-3-ol (98 mg, 0.22 mmol) in THF (1.5 mL) at 0° C. was added NaH (60% in oil, 13 mg, 0.33 mmol) and the suspension stirred for 10 minutes. MeI (26 μL, 0.26 mmol) was added dropwise and the reaction was warmed to room temperature. After one hour the reaction was quenched with saturated aq NH4Cl, partitioned between brine and EtOAc, separated, and the aq layer was extracted with EtOAc (5×). The combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (20 to 50% EtOAc/hexanes) to give the title compound (67 mg, 65%).

Provenance & Evidence