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

HRID 642866

반응식

HRID 642866 반응식
[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

참가 물질

4

반응물 2

HCID 7860Glyoxal2회HCID 27344206-Methylpyridine-2,3-diamine

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4c7e2e3adbee40c18e0e54e255a524e9
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696210B2

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