Sodium hydride → 4-(benzyloxy)-1-(cyclobutylmethyl)-2(1H)-pyridinone

HRID 601430Notes

Reaction equation

HRID 601430 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:19][CH:20]1[CH2:23][CH2:22][CH2:21]1>CN(C)C(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:19][CH:20]2[CH2:23][CH2:22][CH2:21]2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734658(Bromomethyl)cyclobutaneHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 670637964-(benzyloxy)-1-(cyclobutylmethyl)-2(1H)-pyridinoneYield 53.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-benzyloxy-1H-pyridin-2-one (0.60 g, 2.98 mmol) in N,N-dimethylacetamide (10 mL) at 0° C. was treated with sodium hydride (0.086 g, 3.58 mmol) for 30 min, then bromomethyl cyclobutane (0.40 mL, 3.58 mmol) was added and the mixture was stirred at 25° C. for 48 hours. The solution was partitioned between 10% aqueous ammonium chloride solution and dichloromethane, the organic layer was separated, concentrated under reduced pressure and the residue was chromatographed on silica gel, eluting with 1% methanol in dichloromethane to provide the title compound (0.426 g, 53%).

Workup

  1. customThe solution was partitioned between 10% aqueous ammonium chloride solution and dichloromethane
  2. customthe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was chromatographed on silica gel
  5. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-c0fc65517b804863b14b650ca87611f5
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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