2-(Dimethylamino)ethanol → (2R,3R,4S,5R)-2-{2-{[2-(Dimethylamino)ethoxy]methyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

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Reaction Steps

Potassium tert butoxide (112 mg, 1 mmol) was added to a stirred solution of {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (200 mg, 0.25 mmol) (preparation 16) and 2-(N,N-dimethylamino)ethanol (0.16 ml, 1.5 mmol) in N,N-dimethylformamide (3 ml). The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (30 ml) after 30 min. The aqueous phase was extracted with dichloromethane (60 ml). The organic phase was separated, dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure to give a residue that was azeotroped with toluene to remove traces of N,N-dimethylformamide. This was then purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (94:5:1) increasing in polarity to (84:14:2) to give the title compound (33 mg) as a foam. MS: 563 (MH+).

Provenance & Evidence