Potassium Carbonate → HCID 59460393, compound

Participants

Reaction Steps

To a solution of 2′,3′,5′-tris-O-(tert-butyl-dimethylsilyl)-8-(2′-hydroxybiphenyl-4-ylmethylamino)-adenosine (0.313 g) in N,N-dimethylformamide (1.9 mL) was added potassium carbonate (0.080 g). Then methyl bromoacetate (0.048 mL) was added, and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was partitioned between diethyl ether (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (0.337 g) was dissolved in methanol (1.7 mL). Ammonium fluoride (0.379 g) was added, and the resulting mixture was stirred at 60° C. for 19 hours. The reaction mixture was cooled to room temperature. Dichloromethane (10 mL) was added, and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.053 g).

Provenance & Evidence