[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[N:13]=[C:14]([NH:18][C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[N:15]=[C:16]([NH2:17])[C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH:38]([N:41]=[C:42]=[O:43])([CH3:40])[CH3:39].C(OCC)(=O)C>O1CCCC1>[NH2:17][C:16]1[C:11]2[S:10][CH:9]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:42]([NH:41][CH:38]([CH3:40])[CH3:39])=[O:43])[CH:7]=[CH:6][CH:5]=3)[C:12]=2[N:13]=[C:14]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[N:15]=1The 7-(3-aminophenyl)-N2-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-2,4-diamine (20 mg, 0.047 mmol) synthesized in Example 11 was dissolved in anhydrous tetrahydrofuran (1 mL) and then triethylamine (20 μL, 0.14 mmol) and isopropyl isocyanate (5 mg, 0.057 mmol) were added. After stirring at room temperature for 4 hours, ethyl acetate (2 mL) was added and the mixture was washed with brine. After drying with MgSO4, the product was filtered and concentrated. Purification by silica gel chromatography (ethyl acetate/hexane, 1/1) yielded the target compound of Example 12 (18 mg, 75% yield).
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