I[C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.C(=O)(O)[O-].[Na+].[CH3:14][O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[C:19](B(O)O)=[CH:18][N:17]=1>COCCOC.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][C:5]1[N:6]=[C:2]([C:19]2[C:20]([O:22][CH3:23])=[N:21][C:16]([O:15][CH3:14])=[N:17][CH:18]=2)[S:3][C:4]=1[CH3:8]2-iodo-4,5-dimethyl-1,3-thiazole (prepared in a similar manner to that described in JACS 123 (6), 1017-1022, (2001), 250 mg, 1.046 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (4.357 ml). Tetrakis(triphenylphosphine)palladium(0) (60.4 mg, 0.052 mmol) was added and the mixture was stirred at room temperature for 10 minutes. Sodium bicarbonate (4.183 ml, 4.18 mmol) and [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (385 mg, 2.091 mmol) were added and the resulting mixture was stirred at 85° C. for 2 hours. The mixture was allowed to cool to rt and left standing at rt over the week end. The mixture was diluted with DCM (5 mL), the aqueous phases was separated and extracted with DCM (2×5 mL). The organics were combined and dried over sodium sulphate to give a yellow solid that was purified by silica chromatography, eluting with DCM:MeOH from 100:0 to 95:5 to afford the title compound as a pale yellow solid (143 mg).
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