[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[NH:8]2.[H-].[Na+].Br[CH2:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22]>CN(C)C=O.O>[CH2:4]([CH:3]([CH2:12][CH3:11])[CH2:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[N:8]2[CH2:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:5]
To a solution of 5-methoxy-3-methylquinazoline-2,4(1H,3H)-dione (47 mg, 0.228 mmol) [example 5] in N,N-dimethylformamide (1 ml) was added sodium hydride (8.6 mg, 0.342 mmol). The mixture was stirred at 80° C. for 15 min and 1-bromo-2-ethylbutane (0.064 ml, 0.0753 mmol) was added. The resulting mixture was stirred at 80° C. for 18 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting 50% ethyl acetate/n-hexane to afford 20 mg (32%) of 1-(2-ethylbutyl)-5-hydroxy-3-methyl-2,4(1H,3H)-dione (A) and 9 mg (11%) of 5-(2-ethylbutoxy)-1-(2-ethylbutyl)-3-methylquinazoline-2,4(1H,3H)-dione (B).
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