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

HRID 426269Notes

Reaction equation

HRID 426269 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-66560444295b4d7b9f50c344c6dc2bb8
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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