Triethylamine → 5,6-Diphenyl-2-pyrazinamine

HRID 1821776Notes

Reaction equation

HRID 1821776 reaction equation
[N:1]([C:4]1[CH:9]=[N:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=1)=[N+]=[N-].C(N(CC)CC)C.[H][H]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:9]=[N:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118078532-Azido-5,6-diphenylpyrazineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 110860905,6-Diphenyl-2-pyrazinamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-Azido-5,6-diphenylpyrazine (45 mg, 0.17 mmol) in 50 mL EtOAc at room temperature was added triethylamine (100 μL) followed by Pearlman's Catalyst (50 mg). The suspension was put through a vacuum/purge cycle three times with hydrogen gas and then held under I atmosphere of hydrogen for 2 hours. The suspension was then filtered through GF/F filter paper with EtOAc and concentrated. The crude product was eluted through a Biotage 12S column with 1/1 EtOAc/hexane to give pure product, as a clear oil (25 mg, 59%)., 1H-NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.42-7.20 (m, 10H), 4.62 (br s, 2H).

Workup

  1. filtrationThe suspension was then filtered through GF/F
  2. filtrationfilter paper with EtOAc
  3. concentrationconcentrated
  4. washThe crude product was eluted through a Biotage 12S column with 1/1 EtOAc/hexane
  5. customto give pure product

Sources & evidence

ORD record
ord-532ff60f9f9b4fb0a2160695092ff39a
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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