Sodium Azide → 2-Azido-5,6-diphenylpyrazine

HRID 1821775Notes

Reaction equation

HRID 1821775 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C.CCOC(C)=O>[N:20]([C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1)=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 36544935-Chloro-2,3-Diphenylpyrazine

Product 1

HCID 118078532-Azido-5,6-diphenylpyrazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-Chloro-5,6-diphenylpyrazine (45 mg, 0.17 mmol) in 500 μL DMF at room temperature under nitrogen was added sodium azide (11 mg, 0.17 mmol) and the reaction was warmed to 100° C. After stirring overnight, the reaction was cooled to room temperature, diluted with EtOAc (30 mL) and washed 4×30 mL with H2O and 1×30 mL with saturated NaCl. The organics were isolated, dried (MgSO4), filtered and concentrated to the 2-azidopyrazine, which exists as a yellow solid (45 mg, quantitative). 1H-NMR (400 MHz, CDCl3) δ 9.73 (s, 1H), 7.58-7.42 (m, 6H), 7.36-7.23 (m, 4H).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. washwashed 4×30 mL with H2O and 1×30 mL with saturated NaCl
  3. customThe organics were isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to the 2-azidopyrazine, which

Sources & evidence

ORD record
ord-f18b03d7a188453c8704352f1bb077df
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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