N,N-Diethylethanamine trihydrofluoride → 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 532 μL (3.3 mmol, 5 eq.) of triethylamine trihydrofluoride. The reaction was heated to 50° C. for 18 hours. On disappearance of the starting material as indicated by LC analysis, the reaction was allowed to cool which resulted in precipitation of a white solid. This was collected by filtration, rinsed with 3 mL of methanol and dried to provide 171 mg (62%) of the desired product as a white solid.

Provenance & Evidence