Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C:10]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:9]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1)=[CH2:10]A mixture of 6-chloropyrimidin-4-amine (6.5 g, 0.050 mol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (9.24 g, 0.060 mol), tetrakis(triphenylphosphine)-palladium(0) (3.9 g, 0.0030 mol) and sodium carbonate (21 g, 0.20 mol) in dioxane (300 mL) and H2O (30 mL) was stirred at 90° C. under nitrogen for 15 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc (400 mL) and water (150 mL). The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with DCM/MeOH (20:1) to give the desired product as a white solid (4.8 g, 80% yield). LCMS (ESI) m/z: 122.1 [M+H+].
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