(NZ)-2-methyl-N-[[2-(trifluoromethyl)pyrimidin-5-yl]methylidene]propane-2-sulfinamide → 2-Methyl-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}propane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-N-{(1Z)-[2-(trifluoromethyl)pyrimidin-5-yl]methylene}propane-2-sulfinamide (14.3 g, 51.2 mmol) in toluene (260 mL) at −70° C. was added methyllithium (1.6 M; 35.0 mL, 56.0 mmol). The mixture was stirred at −70° C. for 15 min. The mixture was quenched with sat. NH4Cl and the reaction was allowed to warm to ambient temperature. The mixture was extracted with dichloromethane (3×). The combined organic extracts was dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→35% hexanes/ethyl acetate then 100% ethyl acetate→94% ethyl acetate/methanol) gave the title compound (7.23 g). MS 240.0 [(M+1)-56].

Provenance & Evidence