Methanol → HCID 69177935, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-2′,3′,5′-tris-O-(isopropyldimethylsilyl)adenosine (Example 5, 5.0 g, 6.5 mmol) and 15 ml of 2-(4-chlorophenyl)ethyl alcohol was placed under a nitrogen atmosphere and heated to 50° C. Sodium hydride (1.30 g, 60% dispersion in mineral oil, 32.5 mmol) was added at a rate so as to control gas evolution. The reaction was then heated for 48 h at which time LC showed conversion to the fully deprotected coupling product. The reaction was allowed to cool to room temperature, carefully quenched with 40 mL of water and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (120 mL), dried over MgSO4, and concentrated under reduced pressure to afford a clear oil. Chromatography on silica gel eluting with CH2Cl2, 5% MeOH in CH2Cl2, and then 10% MeOH in CH2Cl2 provided 570 mg (20.8%) of the title compound as a white solid. m.p. 158–161° C.

Provenance & Evidence