Sodium Hydroxide → tert-butyl (3-(5-methyl-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

Participants

Reaction Steps

At RT, tert-butyl (3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (54) (440 mg, 1.10 mmol) in DCM (10 mL) was treated with MCPBA (75 wt. %, 681 mg, 2.76 mmol) and stirred for 90 min. The reaction mixture was diluted with DCM (25 mL), treated with ice and 1 N NaOH (30 mL). The DCM layer was separated and the aqueous layer was extracted with an additional amount of DCM (2×20 mL), dried over Na2SO4 and concentrated to furnish tert-butyl (3-(5-methyl-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (451 mg, 1.05 mmol, 95% yield) as an off-white foam. The crude material was used without purification. m/z (ESI, +ve ion) 453.0 (M+Na)+. 1H NMR (400 MHz, CDCl3) δ ppm 9.11 (1H, s), 7.60 (1H, br. s.), 7.45 (1H, t, J=8.0 Hz), 7.23 (1H, dt, J=8.2, 1.0 Hz), 6.91 (1H, ddd, J=7.9, 1.9, 0.8 Hz), 6.80 (1H, d, J=1.4 Hz), 6.60 (1H, s), 3.04 (3H, s), 2.60 (3H, d, J=1.2 Hz), 1.49 (9H, s).

Provenance & Evidence