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

HRID 2362800Notes

Reaction equation

HRID 2362800 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. Subsequently, the reaction mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude residue was then triturated with diethyl ether 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. filtrationSubsequently, the reaction mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was then triturated with diethyl ether

Sources & evidence

ORD record
ord-2c097817f17441b3b621a0d9115c444b
Source dataset
uspto-grants-2014_04
Patent number
US08691849B2

Reaction notes

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