4-(4-bromophenyl)-2,6-diphenylpyrimidine

General procedure: A round bottom flask was charged with the substitutedchalcone 1 (1.0 mmol), benzamidine 2 (1.0 mmol), triethylamine(2.0 mmol) and acetonitrile (10 mL). The mixturewas heated to 80 °C for 4-14 h, and then cooled to r.t.Evaporation of the solvent gave a crude reaction mixture, towhich water (10 mL) was added and the resulting mixturewas extracted with EtOAc (3 20 mL). The combined organiclayer was washed with 1N HCl (20 mL), brine anddried over anhydrous Na2SO4. The solvent was concentratedunder reduced pressure and residue obtained was purified bysilica gel column chromatography (100-200 mesh) using nhexane:Et2O (95:05) as the eluent to afford the correspondingpyrimidine 3.Nineteen grams (67 mmol) of 3-(4-bromo-phenyl)-1-phenyl-propenon obtained in the above step (1) was dissolved in 150 milliliter of ethanol. The resultant solution was mixed with 10.6 g (69 mmol) of benzamidine hydrochloride and 5.5 g (138 mmol) of sodium hydroxide, and the resultant suspension was refluxed under heating for 12 hours. After completion of the reaction, the solution was cooled down to room temperature, then, precipitated crystals were separated by filtration and washed with water and methanol, thereby obtaining 15.9 g of 4-(4-bromo-phenyl)-2, 6-diphenyl-pyrimidine (yield: 61 percent).The intermediate body 2-1 (20 g, 69.7 mmol) and benzamidine hydrochloride (10.8 g, 69.7 mmol) were added to ethanole (300 mL). Sodium hydroxide (5.6 g, 140 mmol) was further added thereto and heated to reflux at room temperature for 8 hours. A precipitated solid was separated by filtration. Then, the obtained solid was washed with hexane. A white solid intermediate body 2-2 (10.3g, a yield rate 38percent) was obtained.General procedure: Intermediate 1 (20g, 69.7 mmol) and benzamidine hydrochloride (10.8g, 69.7 mmol) were added to ethanol (300 mL) and sodium hydroxide (5.6g, 140 mmol) was further added. The mixture was heated under reflux for 8 hours. The precipitates were separated by filtration and washed with hexane to obtain white solids (10.3g, yield 38percent). The solids were identified as Intermediate 2 by FD-MS analysis.The intermediate 4-1 (20 g, 69.7 mmol) and benzamidine hydrochloride (10.8 g, 69.7 mmol) were added to ethanol (300 mL). Sodium hydroxide (5.6 g, 140 mmol) was further added thereto and heated to reflux at room temperature for eight hours. A precipitated solid was separated by filtration. Then, the obtained solid was washed with hexane. A white solid intermediate 4-2 (10.3 g, a yield rate 38percent) was obtained.3.5 g (17.58 mmol) of 4-bromoacetophenone and 1.83 g (17.58 mmol) of benzonitrile were added to 49 mL of dichloromethane cooled at 0° C. by ice bath and stirred for 30 minutes. Then, 10.51 g (35.17 mmol) of antimony (V) chloride was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for about 1 hour and further stirred and refluxed overnight. The reaction mixture was cooled and filtered, and a collected yellow solid was washed with dichloromethane. The solid was slowly added to 75 mL of a 28percent ammonia solution cooled at 0° C. by ice bath and stirred for 30 minutes. Then the reaction mixture was stirred for 3 hours at room temperature. Subsequently, the mixture was filtered, and a white solid was collected. The white solid was then washed with water. Then the solvent was removed under vacuum, and 6.5 g (95percent) of Intermediate 1d was obtained as a white solid.4-bromobenzaldehyde (18.5 g, 100 mmol), acetophenone (12.0 g, 100 mmol), 1N-sodium methoxide/methanol solution (10 ml) and ethanol (200 ml) were stirred at room temperature for 5 hours at the room temperature under an Ar gas atmosphere. Subsequently, the reactant mixture was heated and stirred for another four hours at a reflux temperature. Next, benzamidine hydrochloride (9.4 g, 60 mmol) and sodium hydroxide (8.0 g, 200 mmol) were added thereto and stirred for five hours at 70 degrees C. After the reaction, the reactant mixture was filtered to separate an extract. The extract was refined by silica-gel column chromatography (a developing solvent: dichloromethane) to provide an intermediate body X107.7 g (0.5 mol) of 4-bromoacetophenone and 50.0 ml (0.5 mol) of benz-aldehyde are initially introduced, and 815 ml of sodium hydroxide solution (2 mol/l, 1.6 mol) and 850 ml of DI water are added. A 150 ml three-necked flask was charged with 0.01 mol of Compound A1, 0.01 mol of Compound B1, and 30 ml of Cholinehydroxide ((hydroxyethyl)trimethylammonium hydroxide). Heat to 60 ° C, after the reaction is completed, cool to room temperature. After adding 60 ml of distilled water, suction filtration, the filter cake was rinsed twice with analytically pure ethanol, and passed through a silica gel column to obtain Intermediate C1, purity 99.10percent, yield 62.6percent.

Molecular Weight:387.3
XLogP3:5.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:386.04186
Monoisotopic Mass:386.04186
Topological Polar Surface Area:25.8
Heavy Atom Count:25
Complexity:395
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes