[CH2:1]([N:8]1[C:13](=[O:14])[C:12](Br)=[CH:11][N:10]=[C:9]1[S:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:21]2[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([F:18])[CH:20]=2)=[CH:11][N:10]=[C:9]1[S:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1In a separate flask, 3-benzyl-5-bromo-2-(methylthio)pyrimidin-4(3H)-one (580.5 mg, 1.87 mmol), tris(dibenzylideneacetone)dipalladium (0) (65.0 mg, 0.0710 mmol), 3-fluoro-4-methoxyphenylboronic acid (492.3 mg, 2.90 mmol), S-Phos (97.7 mg, 0.238 mmol), and potassium phosphate (1.250 g, 5.89 mmol) were suspended in toluene (15 ml) and nitrogen was bubbled through for about 30 seconds. The flask was fitted with a reflux condenser and placed in a preheated oil bath (100 C) and stirred under nitrogen for 105 minutes. The reaction was then cooled to room temperature and allowed to stand overnight.
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