Glyoxal → 7-bromopyrido[2,3-b]pyrazine

HRID 642861Notes

Reaction equation

HRID 642861 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:10]([CH:12]=O)=O>CO>[Br:1][C:2]1[CH:7]=[N:6][C:5]2=[N:8][CH:10]=[CH:12][N:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 42469437-bromopyrido[2,3-b]pyrazineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-pyridine-2,3-diamine (6.5 g, 35 mmol) was dissolved in MeOH (100 ml). Glyoxal (15 ml of a 40% solution). The solution was stirred for 18 h at room temperature. The solvent was removed, and the crude material was partitioned between ethyl acetate and brine. The ethyl acetate was washed two additional times with brine, the organic layer was dried using MgSO4, and the solvent as removed to yield the title product (6.9 g (95%),33 mmol). 1H NMR (DMSO-d6): δ=9.28 (d, 1H, J=2.5 Hz), 9.19 (d, 1H, J=1.7 Hz), 9.10 (d,1H, J=1.7 Hz), 8.94(d,1H, J=2.5 Hz). Calculated mass=210.03, [M+H]+=212.

Workup

  1. customThe solvent was removed
  2. customthe crude material was partitioned between ethyl acetate and brine
  3. washThe ethyl acetate was washed two additional times with brine
  4. customthe organic layer was dried
  5. customthe solvent as removed

Sources & evidence

ORD record
ord-692d9b4809e343758b6c60dc3f08e026
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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