5-PHENYL-PYRIMIDINE

General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3×15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh).General procedure: A mixture of aryl halide (0.5 mmol), potassium aryltrifluoroborate (0.6 mmol), K2CO3 (1.0 mmol), Pd/C (5%; 0.5 mol%), ethanol (3 mL), and distilled water (1 mL) was stirred at 80 C in air for the time indicated. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (4×15 mL). The organic solvent was removed under vacuum, and the product was isolated by short-column chromatography.General procedure: In the reaction flask, arylsulfonylhydrazide (1 mmol), phenyldiazonium salt (1.1 mmol), TBAI (1.5 mmol), KOAc (2.0 mmol), PdCl 2 (0.05 mmol), ligand Dcypm (0.1 mmol) and 2 mL DMSO, then heated to 100 C The reaction was carried out. After 12 hours of reaction, the reaction was completely monitored by TLC, cooled to room temperature, and the solid was filtered, and 1 mL of water was added and then extracted with 2 mL of diethyl ether. After taking three times and combining the extracts to dry the solvent, the column was separated by using a mixed solvent of petroleum ether and ethyl acetate as an eluent. That is the product. The reaction formula and reaction results are as follows:General procedure: The metal-free arylations of N-heteroaromatic compounds 1 using (trimethoxybenzene)iodonium salts Iwere performed according to the literature procedure.10a In the case of pyrazine 1d, the iodonium salt Ia(104 mg, 0.2 mmol) and sodium hydroxide (ca. 60 mg, 7.5 equiv) were added to pyrazine solution (1 mL)in reflux tube. After stirring at 110 C for 10 h, the remaining pyrazine was distilled by rotary evaporatorunder reduced pressure. The resulting oily residue including the pheylation product 2da was diluted withEtOAc (20 mL), and washed with brine (15 mL) and water (15 mL), and then the organic layer was driedover anhydrous sodium sulfate. After removal of the solvent, the crude product was subjected to columnchromatography on silica-gel (hexane/EtOAc = 5/1) to give a pure 2-phenylpyrazine 2da (26.8 mg, 0.17mmol) in 86% yield as a colorless crystals.

Molecular Weight:156.18
XLogP3:1.8
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