Tetrahydrofuran → 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 3.27 mL of a 1.0 M solution of TBAF in THF (5 equiv). The reaction was heated to 50° C. for 48 hours. Upon disappearance of the starting material as indicated by LC/MS analysis, the reaction mixture was allowed to cool to room temperature and was concentrated to dryness. Ethyl acetate (20 ml) and water (20 ml) were added and stirred for 5 minutes. The layers were separated and the aqueous layer reextracted with ethyl acetate (2×20 ml). The organic phases were combined, dried over MgSO4 and concentrated to give an oil. The crude material was then purified on silica gel, eluting with a gradient of 0%-10% methanol in CH2Cl2, affording 128 mg (46%) of the desired product as a white solid.

Provenance & Evidence