Dimethylformamide → 3-(5-Dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile
Reaktionsgleichung
C([CH:3]([C:13]1[C:18]([N:19]([CH3:21])[CH3:20])=[C:17]([O:22][CH3:23])[N:16]=[C:15]([O:24][CH3:25])[N:14]=1)[C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:7]#[N:8])#N.[H-].[Na+].CN(C=[O:32])C>>[CH3:20][N:19]([CH3:21])[C:18]1[C:13]([C:3]([C:4]2[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=2)[C:7]#[N:8])=[O:32])=[N:14][C:15]([O:24][CH3:25])=[N:16][C:17]=1[O:22][CH3:23]Komponenten
4
Versuchsvorschrift
To a solution of 3-[cyano-(5-dimethylamino-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-benzonitrile (0.0872 g, 0.258 mmol) in DMF (1.0 mL) was added 60% sodium hydride (0.0114 g, 0.284 mmol) and stirred for 30 min. Oxygen was bubbled into reaction mixture overnight. The reaction was quenched with saturated ammonium chloride solution. The pH was adjusted to ˜6.0 with 1N HCl and mixture was extracted with ethyl acetate. The organic layer was washed with water (2×), dried (MgSO4) and concentrated to give a yellow solid (0.0834 g, 99%). 1H NMR (300 MHz, CDCl3): δ 7.91 (s, 1H), 7.85 (s, 1H), 7.64 (s, 1H), 4.08 (s, 3H), 3.93 (s, 3H), 2.53 (s, 6H), 2.44 (s, 3H). Mass spectrum: 327.2 (M+H)+.
Aufarbeitung
- customOxygen was bubbled into reaction mixture overnight
- customThe reaction was quenched with saturated ammonium chloride solution
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with water (2×)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-66560444295b4d7b9f50c344c6dc2bb8
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08106064B2
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