Morpholine → N-(2-Bromo-4-(1-Methylethyl)Phenyl)-N-Ethyl-4-Methyl-6-(4-Morpholinylcarbonyl)-2-Pyrimidinamine

Participants

Reaction Steps

To sodium hydride (60% in oil, 0.24 g, 6.0 mmol) suspended in anhydrous THF (10 mL) was added morpholine (0.52 g, 6.0 mmol) with stirring; the reaction mixture was warmed to reflux temperature and stirred for 1 hour. The reaction mixture was then cooled to ambient temperature and 2-(N-(2-bromo-4-(2-propyl)phenyl)-N-ethylamino)-4-carbomethoxy-6-methyl-pyrimidine (2.0 g, 5.1 mmol) was added. Stirring was continued for 26 hours. The reaction mixture was then poured onto a 1N NaOH solution, stirred and extracted three time with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Column chromatography (Et2O) afforded the title compound as a solid (900 mg, 39% yield): mp 145° C.; NMR (CDCl3, 300 MHz):d 7.5 (d, 1H, J=1), 7.2 (dd, 1H, J=7,1), 7.1 (d, 1H, J=7), 6.8 (br s, 1H), 4.3-4.15 (m, 1H), 3.9-3.3 (m, 11H), 3.1-3.0 ( m, 1H), 2.9 (septet, 1H, J=7), 1.3 (d, 6H, J=7), 1.15 (t, 3H, J=7); Anal. (C21H27BrN4O2) Calcd: C, 56.38; H, 6.08; N, 12.52; Br, 17.86; Found: C, 56.07; H, 6.05; N, 12.29; Br, 18.08.

Provenance & Evidence