C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.[OH:19][CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:17]([C:14]1[CH:13]=[N:12][C:11]([C:26]2[CH:27]=[CH:28][C:23](/[CH:22]=[CH:21]/[CH2:20][OH:19])=[CH:24][CH:25]=2)=[N:16][CH:15]=1)[CH3:18]1 M aq. Na2CO3 (2 mL), and ethanol (1 mL) were successively added to a mixture of 2-chloro-5-ethylpyrimidine (0.30 mL, 2.47 mmol), [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (61 mg, 0.10 mmol) and [4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic acid (360 mg, 2.02 mmol, prepared as described in Reference Example 238) in toluene (4 mL) and the resulting mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate (10 mL) and the organic layer was separated, washed with brine (10 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) provided 220 mg (45%) of the title compound as a yellow solid. MS 241 (M+H)+.
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