Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH3:8][O:9][C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13](B(O)O)=[CH:12][N:11]=1.O.C([O-])(O)=O.[Na+]>COCCOC.ClCCl>[CH3:8][O:9][C:10]1[N:15]=[C:14]([O:16][CH3:17])[C:13]([C:2]2[N:3]=[C:4]([CH3:7])[S:5][CH:6]=2)=[CH:12][N:11]=14-bromo-2-methyl-1,3-thiazole (commercially available from Frontier, 300 mg, 1.685 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (97 mg, 0.084 mmol) was added and the reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 651 mg, 3.54 mmol) and 1M/H2O sol. of NaHCO3 (4.60 ml, 4.60 mmol) were added thereto. The reaction mixture was heated at 90° C. for 2.5 h and left at room temperature overnight. The mixture was then diluted with dichloromethane (20 ml) and washed with water (20 ml). The organic layer was separated through an hydrophobic frit and concentrated. The obtained crude was purified by flash chromatography eluting with Cyclohexane/AcOEt 8/2. 290 mg of the title compound were isolated as a white solid.
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