Sodium hydride → 5-Bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrazin-2(1H)-one

HRID 1878763Notes

Reaction equation

HRID 1878763 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178516739HCID 178516739, compound

Product 1

HCID 598431045-Bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Bromopyrazin-2-ol (1.209 g, 6.91 mmol) was dissolved in DMF (10.0 mL) and sodium hydride (60% in mineral, 530 mg, 13.25 mmol) was added. The reaction flask was put in a water bath and stirred under argon for 15 minutes, and then (2-bromoethoxy)(tert-butyl)dimethylsilane (1.69 mL, 7.93 mmol) was added as a solution in DMF (4.7 mL total volume), followed by a ˜0.5 mL rinse with DMF. The reaction was stirred under argon at room temperature for 2 days. It was then quenched with water (50 mL) and extracted with EtOAc (3×50 mL). The organic extracts were combined, washed with water (4×50 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated. The material was taken on crude to the next step.

Workup

  1. customThe reaction flask was put in a water bath
  2. washrinse with DMF
  3. stirringThe reaction was stirred under argon at room temperature for 2 days
  4. customIt was then quenched with water (50 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. washwashed with water (4×50 mL) and brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-01d808b0981e4c8a954fdc017e1916b9
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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