Potassium Iodide → HCID 86650742, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-2-yl)-1-phenylmethanimine (3.50 g, 17.4 mmol) and 2-(chloromethyl)pyrimidin-4-amine (2.62 g, 18.3 mmol) in acetonitrile (120 mL) were added cesium carbonate (5.67 g, 17.4 mmol) and potassium iodide (289 mg, 1.74 mmol). After stirring 6 h at 60° C., overnight at room temperature, then again 8 h at 60° C., the reaction mixture was diluted with water (150 mL), sat. aq. sodium bicarbonate (50 mL) and extracted with dichloromethane (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 2-[({[(1-methyl-1H-imidazol-2-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-amine as a foamy solid [4.80 g, yield 76%; HPLC/MS: m/z=309 (M+H); log P(Neutral)=1.42].

Provenance & Evidence