Pyridine, hydrofluoride (1:1) → Sonedenoson

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[2-(4-chlorophenyl)ethoxy]-2′,3′,5′-tri-O-(TERT-butyldimethylsilyl)-adenosine (Example 1, 500 mg, 0.654 mmol) in 7 mL of anhydrous methanol flushed with nitrogen was added 323 mg (5 equiv.) of hydrogen fluoride-pyridine. The reaction was heated to 50° C. for 18 hours. Upon disappearance of the starting material as indicated by LC analysis, the reaction was allowed to cool to room temperature, which resulted in precipitation of a white solid. This was collected by filtration, rinsed with 3 mL of methanol and dried to obtain 138 mg (50%) of the desired product as a white solid.

Provenance & Evidence