Water → 2-Methyl-6-(methylsulfonyl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-methylpyridin-3-amine (40.0 g, 214 mmol), sodium methanesulfinate (87.3 g, 855 mmol), copper(I)trifluoromethanesulfonate-benzene complex (10.8 g, 21.4 mmol), and N1,N2-dimethylethane-1,2-diamine(10.8 g, 21.4 mmol) in DMSO (300 mL) was heated at 150° C. for four hours, cooled, and H2O (100 mL) was added. The dark brown solution was extracted with ethyl acetate (6×30 mL). The organic layer was washed with H2O (100 mL) to remove DMSO. The aqueous layer was back extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over Na2SO4, and filtered. After the volume of the filtrate was reduced to about 200 mL under reduced pressure, a solid product was precipitated and collected by filtration to give the title compound (24.0 g, 60%) as a brown powder. Exact mass calculated for C7H10N2O2S: 186.1. Found: LCMS m/z=187.1 (M+H+); 1H NMR (400 MHz, CDCl3) δ 2.44 (s, 3H), 3.13 (s, 3H), 4.66 (bs, 2H), 7.01 (d, J=8.34 Hz, 1H), 7.71 (d, J=8.34 Hz, 1H).

Provenance & Evidence