2-CHLORO-5-PHENYL-PYRIMIDINE

General procedure: Catalyst (2 molpercent), aryl halide (1 equiv.) and NaGeneral procedure: To an Argon-flushed mixture of 5-bromo-2-chloropyrimidine (600 mg, 3.10 mmol), (2-chlorophenyl)- boronic acid (485 mg, 3.10 mmol) and Na2CO3 (493 mg, 4.65 mmol) in 1, 4-dioxane (4 mL)IWater(1.5 mL) was added Pd(PPh3)4 (90 mg, 0.078 mmol) and the mixture was stirred at 90C for 18 h. A white precipitate was formed. Water was added, an off-white precipitate remained. The solid was filtered off, washed with water and air-dried. Purification by column chromatography (silica, 5% -> 25% EtOAc inheptane) gave pyrimidine INT-7 (2) (504 mg, 2.24 mmol, 72%) as an off-white solid.A flask was flushed with nitrogen and charged with 2-chloro-5- phenylpyrimidine (19.1 g, 100 mmol), 2, 2'-(5-methoxy-l, 3- phenylene)bis(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolane) (15 g, 41.7 mmol), Pd(dppf)Cl2 (0.3l g, 0.4 mmol), and K2CO3 (23 g, 166.4 mmol). A mixture of deaerated toluene/ethanol/water (3: 1: 1, 410 mL) was added and the reaction mixture was stirred at reflux temperature under a nitrogen atmosphere for 22 h. After cooling down to ambient temperature, all volatiles were removed in vacuo and the resulting solid was dissolved in chloroform/water. The organic phase was washed with water three times, dried over MgS04 and filtered over a pad of Florisil. After rinsing with additional chloroform, the filtrate was concentrated in vacuo to a minimal volume and n-hexane was added. The resulting off-white precipitate was isolated by suction filtration and washed with n-hexane. Further purification was achieved by precipitation from dichloromethane by addition of n-hexane to afford 12.6 g (73%) of a white solid after drying. F1PLC: 99.8%; GC-MS: m/z = 416.reflux temperature under a nitrogen atmosphere for 46 h. After cooling down to ambient temperature, the resulting precipitate was isolated by suction filtration and washed with n-hexane. The obtained white solid was dissolved in dichloromethane and washed with water three times. After drying over MgS04, the organic phase was filtered over a pad of Florisil. After rinsing with additional dichloromethane, the colorless filtrate was concentrated in vacuo to a minimal volume and n-hexane was added. The resulting white precipitate was isolated by suction filtration and washed with n-hexane. Further purification was achieved by trituration with n- hexane/dichloromethane (9:1) and recrystallization from toluene to afford 8.6 g (78%) of a white solid after drying. Final purification was achieved by sublimation. F1PLC: 99.8%; ESI-MS: m/z = 579 ([M+H]+).

Molecular Weight:190.63
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:190.0297759
Monoisotopic Mass:190.0297759
Topological Polar Surface Area:25.8
Heavy Atom Count:13
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes