Nitrogen → 2,6-dimethyl-3-(3-morpholinophenyl)pyrimidin-4(3H)-one

Beteiligte Stoffe

Reaktionsschritte

To a solution of 3-morpholinylaniline (3.42 g, 19.20 mmol) in CH2Cl2 (100 mL) was added trimethylaluminum (96 mL, 96 mmol, 1 M in toluene) carefully under N2. The reaction mixture was stirred at rt for 30 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (3.29 g, 19.20 mmol) in anhydrous CH2Cl2 (50 mL). The reaction mixture was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution (200 mL) and extracted with CH2Cl2 (200 mL×3). The combined organic phases were washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (0.73 g, 13%). The compound was characterized by the following spectroscopic data:

Herkunft & Nachweise