4-CHLORO-2,6-DIPHENYLPYRIMIDINE

White solid

Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 mL), 2, 4, 6-trichloropyrimidine (10 g, 54.5 mmol), Pd (PPh3) 4 (3.8 g, 3.27 mmol), K2CO3 (45.2 g, 327 mmol), Water (120 ml) was added And stirred at 90 ° C.After the reaction was completed, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 9.5 g of the product. (Yield: 65percent).Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 mL), 2, 4, 6-trichloropyrimidine (10 g, 54.5 mmol), Pd (PPh3) 4 (3.8 g, 3.27 mmol), K2CO3 (45.2 g, 327 mmol) and water (120 ml). After completion of the reaction, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated.Silica gel column and recrystallization gave 9.5 g of product. (Yield: 65percent).Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 ml), 2, 4, 6-trichioropyrimidine (10 g, 54.5 mmol), Pd(PPh3)4 (3.8 g, 3.27 mmol), K2C03 (45.2 g, 327 mmol), water (120 ml) were added and stirred at 900 C. When the reaction was completed, the reaction mixture was extracted with CH2C12 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallization to obtain 9.5 g of the product (yield:65percent).Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 ml), 2, 4, 6-trichioropyrimidine (10 g, 54.5 mmol), Pd(PPh3)4 (3.8 g, 3.27 mmol), K2C03 (45.2 g, 327 mmol), water (120 ml) were mixed, and then the mixed solution was stirred at 90° C. When the reaction was completed, the reaction product was extracted with CH2C12 and water. And then, the organic layer was dried with MgSO4 and concentrated. Then, the concentrate was separated by silica gel colunm and recrystallized to obtain 9.5 g (yield: 65percent) of the product.Phosphorous oxychloride (9.30 mL, 99. 8 mmol, 7.5 eq. ) was added dropwise to 2, 6-diphenyl-3H-pyrimidin-4-one (10) (3.3 g, 13.3 mmol) in a vigorous reaction. To this mixture was added slowly phosphorous pentachloride (2.77 g, 13.3 mmol, 1 eq. ) and the reaction mixture was stirred at reflux for 3 hours. The reaction mixture was then quenched by pouring into ice-water, and extracted with ethyl acetate (3 x 150 mL). The combined organic layers were washed with water and brine, dried (MgSO4) and then concentrated to give a yellow solid. This was recrystallised from hot ethanol to give fine white needles (65percent). 1H NMR 6 (CDC1s) : 8.60-8. 18 (m, 5H, Ar), 7.63 (s, 1H, Ar), 7. 51-7. 57 (m, 5H, Ar).Ethanol (50 mL) was saturated with NH3 (g) at 0 C and added to 4-chloro-2, 6- diphenyl-pyrimidine (11) (2.30 g, 8.63 mmol) in a sealed vessel. This was then stirred at 140 C for 24 h. Upon cooling and concentrating, the residues were extracted with hot chloroform (3 x 50 mL) and the solvent evaporated in vacuo. The crude product was purified by column chromatography on SiO2 eluting with CH2C12 to give an off-white solid (80%). 1H NMR 8 (DMSO-d6): 8. 47-8. 42 (m, 2H, Ar), 8.16-8. 13 (m, 2H, Ar), 7.57-7. 5 (m, 6H, Ar), 7.02 (br s, 2H, NH2), 6.88 (s, 1H, Ar).Add intermediate 1-1 (30 g, 0.065 mol) to a flask containing 300 ml of tetrahydrofuran and 60 ml of water, and then add

Molecular Weight:266.72
XLogP3:4.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:266.0610761
Monoisotopic Mass:266.0610761
Topological Polar Surface Area:25.8
Heavy Atom Count:19
Complexity:272
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes