Potassium Carbonate → N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide

Participants

Reaction Conditions

Reaction Steps

Steps 2 and 3. To a suspension of N-(3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5a; 5.15 g, 14.63 mmol) in DCM (100 mL) at 0° C. was added MCPBA (77 wt. %, 3.51 g, 15.65 mmol) in one portion. The resulting suspension was stirred at 0° C. for 1 h. The reaction mixture was diluted with DCM (100 mL) and treated with an ice cold solution of 1.0 M K2CO3. The aqueous layer was extracted with DCM (2×100 mL). The organic extracts were dried over Na2SO4, filtered and concentrated affording crude N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5b; 1.09 g, 2.96 mmol, 20% yield) as a light yellow foam. The aqueous layer contained suspended material so it was filtered through a medium porosity sintered glass frit and washed with water and Et2O affording additional N-(3-(5-methyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (5b; 4.59 g, 12.46 mmol, 85% yield) as a light yellow free-flowing solid after drying under vacuum. m/z (ESI, +ve ion) 369.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.33 (1H, s), 9.33 (1H, s), 7.69-7.76 (1H, m), 7.66 (1H, d, J=1.8 Hz), 7.43-7.52 (1H, m), 6.97-7.07 (1H, m), 6.81 (1H, d, J=1.4 Hz), 6.44 (1H, dd, J=16.9, 10.1 Hz), 6.25 (1H, dd, J=16.9, 1.9 Hz), 5.69-5.81 (1H, m), 2.71 (3H, s), 2.59 (3H, d, J=1.2 Hz).

Provenance & Evidence