4-chloro-2-methyl-6-phenylpyrimidine

General procedure: To a degassed solution of4, 6-dichloropyrimidine (200 mg, 1.0 equiv) and arylboronic acid (1.0 equiv) in iPrOH (4 mL) in a 20 mLmicrowave vial was added an aqueous solution of 2M Na2CO3 (2.5 equiv) and Pd(PPh3)4 (5.0 molpercent)under an argon atmosphere and the resulting heterogeneous solution was further degassed for 10 min. Thevial was sealed and placed in an oil bath at 83 oC and the reaction mixture was refluxed for 18 h, cooled, diluted with H2O (20 mL) and the whole was extracted with EtOAc (3 X 30 mL). The combined organicextract was washed with brine, dried (Na2SO4), and evaporated under reduced pressure give an oil whichwas purified by gradient column chromatography on silica gel using EtOAc/hexanes as eluent to affordcompounds 9a-j.Step-2; 4-Chloro-2-methyl-6-phenylpyrimidine; A mixture of 2-methyl-6-phenylpyrimidin-4(3H)-one (15g) and POCl4-Methoxyphenyl)-methyl-(2-methyl-6-phenyl-pyrimidin-4-yl) amine.; [00107] A mixture of ethyl benzylacetate 1.92g (10.0 mmol) and acetamidine hydrochloride 5.Og (53.0 mmol) with a ethanol solution (23percent wt) of EtONa 2OmL (67.5 mmol) was stirred for 36h under reflux. After removal of ethanol, the crude product was extracted with EtOAc, washed with water, and dried on anhydrous MgSOGeneral procedure: A 10-ml Schlenk tube equipped with a stir-bar was charged with compound 1 (0.2 mmol), compound 2 (0.3 mmol), Pd(OAc)2 (0.02 mmol), Xantphos (0.04 mmol), NaOtBu (0.3 mmol), anhydrous DMF (2 mL).The reaction tube was purged with argon. The Schlenk tube was placed in an oil-bath at 110 oC for 36 hours and then cooled to room temperature. The reaction mixture was extracted with EtOAc (3 × 20 mL). The combined organic phase was dried over MgSO4 and concentrated under reduced pressure and the crude residue purified by flash chromatography on silica gel. The purified material was dried in vacuo to afford the corresponding products 3a-w.

Molecular Weight:204.65
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:204.0454260
Monoisotopic Mass:204.0454260
Topological Polar Surface Area:25.8
Heavy Atom Count:14
Complexity:180
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes