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

HRID 426136Notes

Reaction equation

HRID 426136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([O:20][CH3:21])[N:15]=[C:14]([O:22][CH3:23])[N:13]=2)C#N)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].CN(C=[O:30])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[C:17]([CH2:18][CH3:19])=[C:16]([O:20][CH3:21])[N:15]=[C:14]([O:22][CH3:23])[N:13]=2)=[O:30])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59184717HCID 59184717, compound

Product 1

HCID 59184701(3,5-Dichloro-phenyl)-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-methanoneYield 72%

Procedure

To a stirred solution of (62) (1.97 g, 5.59 mmol) in anhydrous DMF (25 ml) under nitrogen atmosphere, was added 60% sodium hydride (224 mg, 5.59 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 (1:30)) to afford 1.37 g (72%) of the title compound as a white solid. m.p. 118-119° C.; 1H NMR (200 MHz, CDCl3) δ 1.09 (3H, t, J=7.4 Hz), 2.46 (2H, q, J=7.4 Hz), 3.95 (3H, s), 4.08 (3H, s), 7.58 (1H, t, J=1.8 Hz), 7.56 (2H, d, J=1.8 Hz).

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 (1:30))

Sources & evidence

ORD record
ord-983c5a503e2c486fb8d32ad73fdd0dac
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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