[CH3:1][C:2]1[N:3]=[C:4]([C:21](=O)[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1[N:3]=[C:4](/[C:21](=[N:26]\[OH:27])/[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1A mixture of 1-[7-methyl-1-(2,4,6-trimethyl-phenyl)-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-5-yl]-propan-1-one (50 mg, 0.154 mmol), hydroxylamine hydrochloride (43 mg, 0.62 mmol), and sodium acetate (57 mg, 0.693 mmol) in ethanol (4 ml) was stirred at room temperature overnight. The mixture was concentrated to dryness, then diluted with water, and extracted with 3 times with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness to give 51 mg of a mixture of the title (E) and (Z)-isomers as a white solid. Both isomers were separated by preparative thin layer chromatography plate with 40% ethyl acetate in hexane as solvent.
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