4-chloro-6-(4'-(trifluoromethyl)phenyl)pyrimidine

General procedure: All solvents and solutions used for this reaction were sparged with argonfor 15 minutes. In a round-bottomed flask was dissolved 4, 6-dichloropyrimidine (1.5 equiv.) inTHF (1 M), under argon atmosphere. The arylboronic acid (1.0 equiv.), palladium acetate (0.02equiv., 2 molpercent), triphenylphosphine (0.04 equiv., 4 molpercent) and 1 M aqueous Na2CO3 solution(2.0 equiv.) were added and the mixture was stirred at 60 °C, overnight. After cooling to roomtemperature, the aqueous layer was extracted with Et2O and the organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated under vacuum. The crude materialwas purified by flash column chromatography to obtain the desired product.2 g (0.011 mol) of 4-trifluoromethylbenzeneboronic acid was weighed out, 4, 6-dichloropyrimidine (1.60 g, 0.011 mol)Tetrakis (triphenyl palladium 0.15g with 2.5 g of anhydrous sodium carbonate was placed in a 120 mL sealed tube, A mixture of tetrahydrofen sitan 30 mL and 20 mL of deionized water was placed in a sealed tube as a solvent, and a stirrer was added and the stopper was capped.The whole device was purged with nitrogen for 3 to 4 times, placed in an oil bath and heated to 120 ° C for about 8 hours with stirring on a magnetic stirrer.After completion of the reaction, the sealing tube was cooled to room temperature, and the solution in the sealed tube was placed in a rotary vial, and the tetrahydrofuran solvent was distilled off under reduced pressure by rotary evaporator. And then extracted with ethyl acetate and water organic products 3 ~ 4 times, vacuum distillation solvent to petroleum ether: ethyl acetate 10: 1 will be steamed after the productionThe samples were separated by column chromatography and separated by separate column chromatography using dichloromethane to give about 1.28 g of a white solid in 47.2percent yield.Example 21 2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-N-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4- ylmethyl] - acetamide A solution of 4-(trifluoromethyl)phenylboronic acid (5.0 g, 25.8 mmol), 4, 6-dichloropyrimidine (3.92 g, 25.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (362 mg, 516 μιηο) and sodium carbonate (8.2 g, 77.4 mmol, Eq: 3) in a three solvent mixture of 50 mL DME, 7.5 mL ethanol and 7.5 mL water was heated at 130°C for 7 h. Upon cooling to rt, the reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with three times with ethyl acetate. The combined organic layers were washed with water and brine and dried over Na2S04. Filtration followed by removal of volatiles under reduced pressure gave a dark red solid. The mixture was purified by flash chromatography (5percent diethyl ether in hexane) to give 4-chloro-6-(4-trifluoromethyl- phenyl)-pyrimidine(2.76g) as a white solid.

Molecular Weight:258.62
XLogP3:3.7
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:258.0171604
Monoisotopic Mass:258.0171604
Topological Polar Surface Area:25.8
Heavy Atom Count:17
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes