Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (1.00 g, 6.22 mmol), 2-fluoro-phenyl-boronic acid (1.04 g, 6.84 mmol), Na2CO3 (790 mg, 7.45 mmol), triphenylphosphine (163 mg, 0.62 mmol) in nPrOH (50 ml), Pd(OAc)2 (42 mg, 0.187 mmol) was added and the mixture was refluxed for 3 hours. The solvent was evaporated under vacuum, and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5) to give the title compound (1.23 g, 90% yield).
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