Pyrimidine,5-bromo-4-methyl-(7CI,8CI,9CI)

To 5-bromopyrimidine (17.3 g, 109 mmol) in diethyl ether (100 mL) , methyllithium in diethyl ether (109 mmol, 1.09 M, 100 mL) was gradually added dropwise at room temperature, and the resulting reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was stirred with water (1.96 mL, 109 mmol) and 2 , 3-dichloro-5 , 6-dicyano-p- benzoquinone (24.7 g, 109 mmol) in tetrahydrofuran (150 mL) at room temperature for 16 hours. After completion of the reaction, water and ethyl acetate were added, and the organic layer was separated. The organic layer was washed with IM aqueous sodium hydroxide, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1) to give the desired product (2.9 g, 15percent yield) . Morphology: yellow oil 1H-NMR(CDClUnder Ar(g), to a mixture of pyrazin-2-amine (1) (151 mg, 1.6mmol), 5- bromo-4-methylpyrimidine (2) (250mg, 1.4mmol), Cs2C03 (0.94g, 2.9mmol) was added degassed dry 1 , 4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (66mg, 0.07mmol) and Xantphos (92mg, 0.16mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15ml_) and H20 (15mL) were added. The organic phase was separated and the water layer was extracted with EtOAc (15ml_). The organic layers were combined and Pd- scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (35mg, 13%).To a sealed tube was added bis(pinacolato)diboron (220 mg, 0.87 mmol), 5- (2-biphenyl) pyrimidine synthesis of methyl 4->5-Bromo-4-methyl pyrimidine 2.9g (16.8mmol), 2- biphenyl boronic acid 3.6g (18.0mmol), tripotassium phosphate 9.6g (45.0mmol), 2- dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (S-phos) 0.369g (0.900mmol), toluene 40mL into 300mL three-necked flask, atmosphere in the flask was replaced with nitrogen, and then under reduced pressure while stirring deaeration. After degassing, atmosphere in the flask was replaced with nitrogen, was added palladium acetate (II) 0.101g (0.450mmol), under a nitrogen flow to 100 deg.] C for 13 h. Of the obtained reaction solution was added water, and the reaction solution was separated into an organic layer and an aqueous layer, and the aqueous layer was extracted with chloroform. With saturated aqueous sodium chloride solution and the organic layer extracted was washed, dried over anhydrous magnesium sulfate and added. The obtained mixture was gravity filtered, and the filtrate was concentrated to give a solid. Silica gel column chromatography of the solid crude product was purified. As a developing solvent, hexane: ethyl acetate = 4: 1 mixed solvent. The obtained target product fraction was concentrated to give 98% yield as a white solid 4.1g, and confirmed using nuclear magnetic resonance (NMR) method to give a white solid of 5- (2-biphenyl) -4 pyrimidine.

Molecular Weight:173.01
XLogP3:1.3
Hydrogen Bond Acceptor Count:2
Exact Mass:171.96361
Monoisotopic Mass:171.96361
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes