Triethylamine → (1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-[6-(phenylethynyl)-9H-purin-9-yl]cyclopentanol

Participants

Reaction Steps

A solution of (1S,2R,4R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(6-chloro-9H-purin-9-yl)cyclopentanol (0.1 g, 0.26 mmol), Pd(PPh3)2Cl2 (0.006 g, 0.0089 mmol), CuI (0.004 g, 0.02 mmol) and triethylamine (0.145 mL, 1.04 mmol) in DMF (5 mL) was heated at 70° C. under argon for 1 h. Phenylacetylene (0.057 mL, 0.52 mmol) was added, the reaction mixture was stirred for 3 h, and the reaction was concentrated. The residue was dissolved in DCM and washed with saturated aq NaHCO3 and saturated aq EDTA.Na2 acid. The organic layer was dried (Na2SO4), concentrated and purified by flash chromatography (0 to 50% EtOAc/DCM) to afford the title compound (0.096 g, 82%).

Provenance & Evidence