Acetonitrile → 4-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-morpholinopropylthio)anilino]pyrimidine

Participants

Reaction Conditions

Reaction Steps

4-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-hydroxypropylthio)anilino]pyrimidine (Method 84; 250 mg, 0.65 mmol) was suspended in DCM (8 ml) and acetonitrile (2 ml) and the stirred at room temperature under nitrogen. Triethylamine (100 μl) was added followed by dropwise addition of methane sulphonyl chloride (50 μl). The mixture was stirred for 2.5 hours and then allowed to stand for 18 hours. The volatiles were removed by evaporation, the residue dissolved in acetonitrile (5 ml), and morpholine (120 μl) and potassium carbonate (50 mg) were added. The mixture was stirred and heated at 80° C. for 3.5 hours and then the volatiles were removed by evaporation. The residue was partitioned between EtOAc (50 ml) and water (20 ml). The aqueous layer was basified to pH 9 with sodium bicarbonate solution. The phases separated and the aqueous layer re-extracted with EtOAc. The extracts were combined, washed with water (10 ml) and brine (10 ml), dried and then evaporated to give the title compound (260 mg, 88%) m/z 453.

Provenance & Evidence