Triethylamine → 2-Amino-5-phenylpyrazine

HRID 1830772Notes

Reaction equation

HRID 1830772 reaction equation
Br[C:2]1[C:3]([NH2:14])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.C(N(CC)CC)C>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[NH2:14][C:3]1[CH:2]=[N:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 124535523-Bromo-5-phenylpyrazin-2-amine

Product 1

HCID 5987342-Amino-5-phenylpyrazineYield 75%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-bromo-5-phenyl-2-amino pyrazine (80 mg; 0.32 mmol), in ethyl acetate (1 mL) was added triethylamine (139 μL; 1.0 mmol) and Pd(OH)2 (10 mg; 20% wt on carbon). The reaction was placed under a hydrogen atmosphere at 45 psi and shook for 6 hours. The reaction was filtered and concentrated under reduced pressure. The product was purified using a biotage 12L eluting with ethyl acetate to yield an off white solid (75% yield).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe product was purified
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b70a0479d4224bcea20ea2a4ed2f9997
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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