Hexane → HCID 89734168, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-trifluoromethyl-pyrimidine (200 mg, 0.879 mmol) in dry diethyl ether (1.5 ml) at −78° C. was added a 2.5 M solution of n-butyllithium in hexane (0.32 ml, 0.811 mmol) and the mixture was stirred at −78° C. for 15 min. A solution of (S)-2-methyl-propane-2-sulfinic acid propylideneamide (Comp. No. 13b) (110 mg, 0.676 mmol) in dry toluene (1 ml) was added at −78° C., the mixture was stirred for 5 min at −78° C. and then poured into a saturated aqueous ammonium chloride solution. The mixture was extracted 3 times with dichloromethane, dried over sodium sulfate, and after evaporation of all solvents the crude product was purified by flash chromatography (silica gel, elution with heptane/ethyl acetate) to give 15 mg of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-(2-trifluoromethyl-pyrimidin-5-yl)-propyl)amide (LC/MS (method 7): Rt=1.37 min; m/z=310.1 (M+H+)) and 20 mg of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-(2-trifluoromethyl-pyrimidin-5-yl)-propyl)amide (LC/MS (method 7): Rt=1.37 min; m/z=310.1 (M+H+)).

Provenance & Evidence