Methyl iodide → HCID 86607298, compound

Participants

Reaction Steps

To a suspension of (6aR,8R,9S,9aS)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol (3.06 g, 5.79 mmol) and Cs2CO3 (18.86 g, 57.9 mmol) in DMF (58 mL) at 0° C. was added methyl iodide (3.60 mL, 57.9 mmol) dropwise and reaction was stirred for 3 h while warming to r.t. The solution was diluted with CH2Cl2 (150 mL) and washed with saturated aq NH4Cl. The aq layer was extracted with CH2Cl2 (2×100 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (5 to 30% EtOAc/hexanes) to afford the title compound (1.51 g, 48%).

Provenance & Evidence