Methyl iodide → 1-Benzoyl-2-methyl-3-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)isothiourea

Participants

Reaction Conditions

Reaction Steps

To a heterogeneous brown mixture of 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (0.260 g, 0.886 mmol) in 2 mL acetone was added benzoyl isothiocyanate (0.136 ml, 0.975 mmol) dropwise via syringe. The mixture became homogeneous and remained brown. After 10 min, a precip formed. After 16 h, iodomethane (0.0554 ml, 0.886 mmol) was added, and the reaction was heated to 80° C. The mixture became homogeneous. After 3 h, further iodomethane (0.0554 ml, 0.886 mmol) was added and after 1 h at 80° C. and 3 days at ambient temperature, the reaction was adsorbed onto 1.7 g SiO2 and dried. The solid was purified by silica gel chromatography, 40 g, 0-10% MeOH/MC, to give 1-benzoyl-2-methyl-3-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)isothiourea which was used without further purification. MS m/z=471 [M+H]+. Calc'd for C25H22N6O2: 470.5.

Provenance & Evidence