2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 3-(4-(diisobutylamino)-3-fluorophenyl)-2,6-dimethylpyrimidin-4(3H)-one

Participants

Reaction Steps

To a solution of 2-fluoro-N1,N1-diisobutylbenzene-1,4-diamine (0.40 g, 1.68 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (8.4 mL, 8.4 mmol, 1 M in heptane) slowly at rt. The reaction mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (290 mg, 1.85 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred at rt for 3 days, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (100 mL×3). The combined organic phases were 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 pale yellow oil (280 mg, 48%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence