Glyoxal → 6-Methylpyrido[2,3-b]pyrazine

HRID 642866

Reaktionsgleichung

Reaktionsgleichung von HRID 642866
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[CH:10]([CH:12]=O)=O>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:7]=1)=[N:8][CH:10]=[CH:12][N:9]=2

Komponenten

4

Edukt 2

HCID 7860Glyoxal2×HCID 27344206-Methylpyridine-2,3-diamine

Produkt 1

HCID 104193166-Methylpyrido[2,3-b]pyrazineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

6-Methyl-pyridine-2,3-diamine (1.01 g, 8.2 mmol) was dissolved in MeOH (40 ml) and glyoxal (14 ml of a 40% aqueous glyoxal solution). Allowed to stir 18 h. The MeOH was removed, and the crude was taken up in ethyl acetate. It was washed three times with a 1 N HCl solution. The combined acid washings were washed twice with ethyl acetate. The acidic water was made basic with the addition of solid sodium carbonate, and it was extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried using MgSO4, and concentrated under vacuum to yield the title product (980 mg, 80%) as a brown solid. 1H NMR (DMSO-d6): δ=9.09 (d, 1H,J=1.8 Hz), 8.99 (d, 1H, J=1.8 Hz), 8.47 (d, 1H, J=8.5 Hz), 7.82 (d, 1H, J=8.5 Hz), 2.78 (s, 3H). Calculated mass=145, [M+H]+=146.

Aufarbeitung

  1. customThe MeOH was removed
  2. washIt was washed three times with a 1 N HCl solution
  3. washThe combined acid washings were washed twice with ethyl acetate
  4. additionThe acidic water was made basic with the addition of solid sodium carbonate, and it
  5. extractionwas extracted three times with ethyl acetate
  6. washThe combined ethyl acetate extracts were washed with brine
  7. customdried
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4c7e2e3adbee40c18e0e54e255a524e9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696210B2

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