C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[C:14]([CH:15]=[O:16])=[C:13]([CH3:17])[C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][CH:10]=1.[Cl:27][C:28]1[N:33]=[C:32](Cl)[CH:31]=[CH:30][N:29]=1.O>C(COC)OC>[Cl:27][C:28]1[N:33]=[C:32]([C:12]2[C:13]([CH3:17])=[C:14]([C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[CH:15]=[O:16])[CH:31]=[CH:30][N:29]=1A 2 M aqueous solution of sodium carbonate (2.72 mL, 5.43 mol) and tetrakistriphenylphosphine palladium(0) (209 mg, 0.181 mmol) were added to a suspension of the 6-methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde obtained in Example 4-1 (500 mg, 1.81 mmol) and 2,4-dichloropyrimidine (405 mg, 2.72 mmol) in dimethoxyethane (5.4 mL) at room temperature. The mixture thus obtained was stirred at 80° C. for 10 hours. Thereafter, the resulting solution was cooled to room temperature. Water was added to the reaction solution, and the precipitated crude product was collected by filtration and was then washed with water and diisopropyl ether to obtain the title compound (418 mg, yield: 88%).
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