Dimethylformamide → 3-(5-Dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 426269노트

반응식

HRID 426269 반응식
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]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 591847233-[Cyano-(5-dimethylamino-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-benzonitrile

생성물 1

HCID 591847653-(5-Dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile수율 99%

실험 절차

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)+.

후처리

  1. customOxygen was bubbled into reaction mixture overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water (2×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-66560444295b4d7b9f50c344c6dc2bb8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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