Water → 6-methyl-N1-(4-morpholinopyrimidin-2-yl)benzene-1,3-diamine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-amino-4-methyl-phenyl) acetamide (5 g, 41 mmol) in DMF (5 ml) was added 4-(2-chloro-pyrimidin-4-yl)-morpholine (8.1 g, 40 mmol) and KI (0.5 g, 3 mmol), which was stirred at 100° C. overnight, cooled to 10° C. and added to H2O (100 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL), the combined organic layers dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h and concentrated in vacuo to yield 6-methyl-N1-(4-morpholinopyrimidin-2-yl)benzene-1,3-diamine hydrochloride (5.0 g, 65%). 1H NMR (DMSO-d6): 8.00 (d, J=7.2 Hz, 1H), 7.57 (brs, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.14 (dd, J=8.4, 1.6 Hz, 1H), 6.65 (d, J=7.2 Hz, 1H), 3.69 (s, 4H), 3.66 (s, 4H), 2.25 (s, 3H). MS (ESI) m/e: 286 (M++1).

Provenance & Evidence