Sodium Iodide → 5-Bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-hydroxypyrimidine (1.00 g, 5.75 mmol) in DMF (19 mL) was added sodium iodide (1.29 g, 8.6 mmol), cesium carbonate (4.68 g, 14.4 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.18 g, 6.32 mmol) and the reaction mixture was stirred at 60° C. for 2.5 h. The solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with gradient of methanol (5-15%) in dichloromethane to give title compound 413 (1.29 g, 78% yield). MS (m/z): 288.1 (50%) (M+H), 290.0 (50%) (M+H). 1H NMR (DMSO-d6) δ (ppm): 8.61 (d, J=3.3 Hz, 1H), 8.46 (d, J=3.3 Hz, 1H), 3.93 (t, J=5.9 Hz, 2H), 3.51 (t, J=4.5 Hz, 4H), 2.57 (t, J=6.1 Hz, 2H), 2.45-2.39 (m, 4H).

Provenance & Evidence