2-PHENYLPYRIMIDINE

2-Phenylpyrimidine General procedure: To a mixture of aryl halide (1 mmol), phenylboronic acid (1.5 mmol) and K2CO3 (1 mmol) in dimethylacetamide (4 mL) was added the catalyst (1 molpercent) as a dimethylacetamide solution (1 mL). The resultant mixture was then heated at 90C for 7 h. Then, the mixture was cooled, water was added and the product was extracted with ethylacetate. The organic layer was washed with brine, dried over Na2SO4, filtered, passed through celite, and analyzed by GC. GC yields were obtained based on corresponding aryl halide. The isolated yield was characterized by 1H NMR.An oven-dried round bottom flask (10 ml) was charged with 0.1ml dimethylformamide solution of complex IV (0.1 mol percent for aryl bromides and 0.2 mol percent for aryl chlorides), aryl boronic acid (1.2 mmol), aryl halide (1.0 mmol), KTo a solution of 2-chloropyrimidine (1.21 g, 10.0 mmol) and Pd(dppf)Cl2(408 mg, 0.5 mmol) in THF (50 mL), triphenylindium (4.0 mmol, ~0.3 M en THF) was added. Themixture was stirred at 80 °C for 4 h and the reaction quenched by addition of drops of MeOH. Thesolvent was evaporated and EtOAc (25 mL) was added. The organic phase was washed with HCl(5percent, 15 mL), satd. NH4Cl (15 mL) and brine (15 mL), dried, filtered, and concentrated. The crudewas purified by flash chromatography (20percent EtOAc/hexane) affording, after concentration and drying, 12 (1.42 g, 9.09 mmol, 91percent) as a white solid. M.p. 36–38 °C (lit. [38], 36–38 °C). 1H NMR (CDCl3, 300 MHz) δ 6.95 (t, J = 4.9 Hz, 1 H), 7.42–7.49 (m, 3 H), 8.47–8.50 (m, 2 H), 8.66 (d, J = 4.9 Hz, 2 H) ppm;13C NMR (CDCl3, 75 MHz) δ 119.0 (CH), 128.2 (2 x CH), 128.6 (2 x CH), 130.8 (CH), 137.5 (C), 157.1(2 x CH), 164.5 (C) ppm; IR (ATR) 3087, 3066, 3039 cm-1; MS (EI) m/z (percent) 156 (M+, 92), 103 (100);HRMS (EI) m/z calcd for C10H8N2 156.0682, found 156.0683.General procedure: Preparation of compound 3a. Compound 2a (1.434 g, 4.001 mmol) was dissolved in DMSO (10 mL), and powdered sodium hydroxide (0.240 g, 6.000 mmol) was added. The mixture was warmed to around 60 C, and then stirred at 60 °C for 4 h. When the reaction was complete (monitored by TLC), the mixture was allowed to cool down to room temperature and then was diluted with water (80mL). The aqueous solution was then extracted twice with ethyl acetate (260 mL). The extracts were combined and dried with anhydrous MgSO4. Evaporation of the solvent gave a residue, which was purified by flash chromatography to furnish pure 2-(3-ethoxyphenyl)pyrimidine 3a (0.641 g, 3.201 mmol) in 80percent yield as colorless oil.General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and KGeneral procedure: To the catalyst (1.0 molpercent) dissolved in 1 ml DMAc, aryl bromide (1.0 mmol), phenyl boronic acid (1.5 mmol) in 1 ml ethanol, KGeneral procedure: Ammonium persulfate (3 equiv, 342 mg), phenylboronic acid (1.5 equiv, 91 mg), silver nitrate (0.2 equiv, 17 mg), and zinc trifluoromethanesulfonate (0.2 equiv, 36 mg) were combined ina 10 mL round bottom flask. A heterocycle (1 equiv, 0.5 mmol) was then added to the same flask and solvated with water (0.4 mL) and CH

Molecular Weight:156.18
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:156.068748264
Monoisotopic Mass:156.068748264
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes