Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine

Participants

Reaction Steps

To a solution of triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH) was added 5′-O-t-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and the resultant mixture was stirred at room temperature for 24 hrs. The reaction was monitored by TLC (5% MeOH in CH2Cl2). The solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to give the title compound (766 mg, 92.5%). Rf 0.27 (5% MeOH in CH2Cl2). MS (FAB⊕) m/e 346 (M+H⊕)

Provenance & Evidence