[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([O:22]CC)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2].[OH:25]O.Cl>O1CCCC1.CO.O.[OH-].[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([OH:22])=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)(=[O:25])[NH2:2]To a solution of ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (C4, 800 mg) in tetrahydrofuran (25 mL) and methanol (25 mL), water (2 mL) and 4.0 mol/L aqueous sodium hydroxide (8 mL) were added at room temperature, and the mixture was stirred at 55° C. for 1 hour and 20 minutes. The reaction mixture was cooled to room temperature, and then 35% aqueous hydrogen peroxide (8 mL) was added to the mixture, and the mixture was stirred at the same temperature for 45 minutes. To the reaction mixture, 3.0 mol/L aqueous hydrochloric acid was added until the reaction mixture was neutralized. The solid matter was taken by filtration, and dried under reduced pressure to obtain 2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid (C2, 500 mg) as white solid.
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