Sodium Bicarbonate → (S)-2-methyl-propane-2-sulfinic acid ((R)-1-pyrimidin-2-yl-propyl)-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-methyl-propane-2-sulfinic acid 1-pyrimidin-2-yl-methylideneamide (18.2 g, 86.1 mmol) in dry tetrahydrofuran at −78° C. was added a 1.0 M solution of ethylmagnesium bromide in tetrahydrofuran (95 ml, 95 mmol) and the mixture was stirred at −78° C. for 45 min. 120 ml of aqueous sodium hydrogencarbonate was added, the mixture was extracted 3 times with dichloromethane (200 ml) and after evaporation of all solvents the crude product was purified by reverse phase HPLC (acetonitrile/water gradient with 0.1% trifluoroacetic acid) to give 1.47 g of (S)-2-methyl-propane-2-sulfinic acid ((S)-1-pyrimidin-2-yl-propyl)-amide (LC/MS (method 5): Rt=2.99 min; m/z=242.21 (M+H+)) and 2.6 g of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-pyrimidin-2-yl-propyl)-amide (LC/MS (method 2): Rt=0.97 min; m/z=242.07 (M+H+)).

Provenance & Evidence