[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:10]1[CH:38]=[CH:37][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]3[N:33]([CH3:34])[C:32](=[O:35])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]=4[CH3:36])[N:25]=3)=[CH:18][CH:17]=2)=[O:15])=[CH:12][N:11]=1>CN(C=O)C>[CH3:34][N:33]1[C:32](=[O:35])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[CH3:36])[N:25]=[C:24]1[CH:23]=[CH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[O:15])[C:13]2[CH:37]=[CH:38][C:10]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:11][CH:12]=2)=[CH:17][CH:18]=1To a solution of 2-dimethylaminoethanol (53 mg) in DMF (3 ml) was added 60% sodium hydride (29 mg) and the mixture was stirred at room temperature for 10 minutes. Then, 2-[2-[4-(6-chloronicotinoyl)phenyl]vinyl]-3,5-dimethyl-4(3H)-quinazolinone (208 mg) was added and the mixture was further stirred at room temperature for 2 hours. This reaction mixture was extracted with ethyl acetate and the organic layer was washed serially with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to 10 ml. To this organic was added 1N-hydrochloric acid (2 ml) and the mixture was extracted with water. The aqueous layer was diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness to provide 169 mg of yellow powder.
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