Hydrogen Peroxide → 5-Trifluoromethyl-2'-deoxycytidine

Participants

Reaction Conditions

Reaction Steps

0.15 g (1.0 mmol) of 2′-deoxycytidine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30% hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyl-2′-deoxycytidine (19F-NMR yield: 11%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethyl-2′-deoxycytidine was obtained as a white solid (0.01 g, yield: 3.3%) by column chromatography.

Provenance & Evidence