Dimethylformamide → (3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

HRID 426133Notes

Reaction equation

HRID 426133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)C#N)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].CN(C=[O:31])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)=[O:31])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59184725(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

Product 1

HCID 59184648(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanoneYield 80%

Procedure

To a stirred solution of (59) (9.6 g, 26 mmol) in anhydrous DMF (100 ml) under nitrogen atmosphere, was added 60% sodium hydride (1.05 g, 26 mmol). After 10 min., oxygen was bubbled into the reaction mixture for 4 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:10)) to afford 7.36 g (80%) of the title compound as a white solid. m.p. 120-121° C.; 1H NMR (200 MHz, CDCl3) δ 1.22 (6H, d, J=7.0 Hz), 2.86 (1H, m), 3.96 (6H, s), 4.09 (3H, s), 7.60-7.74 (3H, m).

Workup

  1. customoxygen was bubbled into the reaction mixture for 4 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:10))

Sources & evidence

ORD record
ord-adb5ff45f1814e4eb84830f1ce00397f
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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