Sodium hydride → tert-Butyl (2-oxo-3-pyridin-2-ylimidazolidin-1-yl)acetate

HRID 458550Notes

Reaction equation

HRID 458550 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[H-].[Na+]>CN(C=O)C>[O:12]=[C:8]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:11][CH2:10][N:9]1[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 2942411-(Pyridin-2-yl)imidazolidin-2-one

Product 1

HCID 86606174tert-Butyl (2-oxo-3-pyridin-2-ylimidazolidin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 1-pyridin-2-ylimidazolidin-2-one from Step A (150 mg, 0.92 mmol) and tert-butyl bromoacetate (197 mg, 1.01 mmol) in DMF (2 mL) at 0° C. was added sodium hydride (40 mg of a 60% dispersion in mineral oil, 1.00 mmol). The mixture was stirred at 0° C. for 30 min, then quenched with saturated aqueous NaHCO3 and extracted with CHCl3 (2×35 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 70:30, to give the title compound. MS: m/z=278 (M+1).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with CHCl3 (2×35 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-27a0f940cc0e46dea7fbc8967dfa1fc9
Source dataset
uspto-grants-2007_03
Patent number
US07192954B2

Reaction notes

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