(3-methylphenyl)methanesulfonyl Chloride → 5-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide

Participants

Reaction Steps

Potassium tert-butoxide (75.9 mg, 676 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (150 mg, 520 μmol) in THF (15.0 ml) and DMF (3 ml). The resulting mixture was stirred for 10 min and then cooled with an ice-bath. To this mixture was slowly added a solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml). The reaction mixture was stirred at room temperature overnight. A further solution of (3-methylphenyl)methanesulfonyl chloride (140 mg, 684 μmol) in THF (1 ml) was added and then the mixture was stirred at room temperature for 48 hours. The resulting mixture was diluted with EtOAc, washed with saturated NaHCO3 aqueous solution and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (silica gel, 0% to 2% MeOH in DCM) provided the desired product as a light yellow solid (0.070 g; 29%). LCMS: m/z=457 (MH+).

Provenance & Evidence