Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[N:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:12]1[CH:11]=[C:10]([NH2:9])[CH:15]=[N:14][CH:13]=1
The mixture of 2-bromopyrimidine (0.76 g, 4.80 mmol), (5-aminopyridin-3-yl)boronic acid hydrochloride (1.00 g, 5.75 mmol), Pd(Ph3P)2Cl2 (0.73 g, 0.96 mmol) and K2CO3 (2.78 g, 20.2 mmol) in dioxane (40 mL) and water (10 mL) was degassed with argon stream. It was stirred at 95° C. in argon atmosphere for overnight. The mixture was concentrated in vacuo to dryness. The solid was triturated with dioxane and EtOAc. The organic solutions were combined, filtered, concentrated and subjected to flash column (0-8% MeOH in DCM) to isolate 5-(pyrimidin-2-yl)pyridin-3-amine (0.24 g).
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