Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C>O1CCOCC1>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:23]3[CH:24]=[C:19]([NH2:18])[CH:20]=[CH:21][CH:22]=3)[C:6]=2[N:7]=1
7-Bromo-2-chlorothieno[3,2-d]pyrimidine (3.645 g, 14.61 mmol) was dissolved in dioxane (44 mL) and 2.0 N sodium carbonate (22 mL, 43.83 mmol) and 3-aminophenylboronic acid (2 g, 14.61 mmol) were added. After flowing nitrogen to the mixture solution for 10 minutes, Pd2(PPh3)Cl2 (615 mg, 0.88 mmol) and t-ButylXphos (558 mg, mmol) were added. The reaction mixture solution was stirred at 90° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was concentrated by drying with magnesium sulfate. Purification by chromatography (20% ethyl acetate/hexane) yielded the target compound (2.8 g, 73% yield).
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