Diisopropylethylamine → [(3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

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Reaction Steps

To a solution of [(3aR,4R,6R,6aR)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate (0.200 g, 0.402 mmol) in DMF (7 mL) was added DIPEA (0.176 mL, 1.01 mmol), 1-ethynyl-2-trifluoromethyl-benzene (0.224 mL, 1.61 mmol), CuI (0.0191 g, 0.101 mmol), and Pd(PPh3)2Cl2 (0.0282 g, 0.0402 mmol). The mixture was stirred at r.t. for 50 min, diluted with DCM (25 mL) and washed with saturated aq EDTA.Na2 (3×25 mL). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography (15 to 50% EtOAc/DCM) to isolate the title compound (0.185 g, 85%).

Provenance & Evidence