Potassium Carbonate → 4-(Benzyloxy)-1-(cyclopropylmethyl)pyridin-2(1H)-one

HRID 404695Notes

Reaction equation

HRID 404695 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][N:23]([CH2:2][CH:3]2[CH2:5][CH2:4]2)[C:22](=[O:26])[CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 594970994-(Benzyloxy)-1-(cyclopropylmethyl)pyridin-2(1H)-oneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromomethyl-cyclopropane (3.68 g, 27.33 mmol) and potassium carbonate (10.3 g, 74.52 mmol) were added to a solution of 4-benzyloxy-1H-pyridin-2-one (5.0 g, 24.84 mmol) in acetonitrile (200 ml) and the mixture was heated at reflux temperature for 16 hours. The reaction mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude residue was then triturated with diethylether to yield pure D1 (6.32 g, 98%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was then triturated with diethylether

Sources & evidence

ORD record
ord-0d02d790849344e191c3d4bce5268431
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Reaction notes

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