Toluene → 3-(4-(dihexylamino)-3-fluorophenyl)-2-((3-fluorophenoxy)methyl)-6-methyl-pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(4-(dihexylamino)-3-fluorophenyl)-3-oxobutanamide (2.67 g, 7.05 mmol), and 2-(3-fluorophenoxy)acetamide (2.37 g, 14.0 mmol) in xylene (20 mL) was added titanium tetraisopropanolate (5.97 g, 21.0 mmol) and the mixture was stirred at 165° C. for 24 h. The mixture was cooled to rt and 120 mL of toluene and 150 mL of saturated NH4Cl aqueous solution were added. The resulting mixture stirred at rt overnight and filtered and the filtrate was extracted with DCM (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (0.95 g, 26%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence