Water → 4-amino-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyridin-2(1H)-one

HRID 1807253

Reaction equation

HRID 1807253 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[H-].[Na+].Br[CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:4](=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 592494614-amino-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyridin-2(1H)-oneYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 4-aminopyridin-2(1H)-one (Molbridge)(0.9 g, 8.17 mmol) in DMF (30 mL) was added NaH (60%, 490 mg, 12.3 mmol). The mixture was stirred at room temperature for 30 min before (2-bromoethoxy) (tert-butyl)dimethylsilane (2.15 g, 8.99 mmol) was added. The reaction mixture was heated at 78° C. for 15 h. The mixture was cooled and poured into H2O (100 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with H2O (5×50 mL), brine (50 mL), dried over MgSO4 and concentrated. The residue was purified by flash chromatography (silica gel, 40+S, 0% to 10% MeOH in EtOAc) to give 4-amino-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyridin-2-one as a white solid (0.9 g, 41%).

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washwashed with H2O (5×50 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, 40+S, 0% to 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-87024fa7600440aeb118822706e1cb31
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Linked notes

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