1-Bromo-3-chloropropane → HCID 67454924, compound

Participants

Reaction Steps

A mixture of 8-[2-(3′-benzyloxybiphenyl-4-yl)ethyl-amino]-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.27 g) and 10% palladium-on carbon (56.2 wt % H2O, 0.12 g) in methanol (5 mL) was stirred at room temperature for 3 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure. To a solution of the residue obtained in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.12 g). Then 1-bromo-3-chloropropane (0.07 mL) was added, and the resulting mixture was stirred at 40° C. for 42 hours. The reaction mixture was partitioned between ethyl acetate (45 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 to give the title compound (0.19 g).

Provenance & Evidence