Water → 7-Bromo-8-methylpyrido[2,3-b]pyrazine

HRID 80557Notes

Reaction equation

HRID 80557 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:11]([CH:13]=O)=O.O>C(O)C.O>[Br:1][C:2]1[CH:7]=[N:6][C:5]2=[N:8][CH:11]=[CH:13][N:9]=[C:4]2[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7860GlyoxalHCID 101251415-Bromo-4-methylpyridine-2,3-diamine

Product 1

HCID 337264357-Bromo-8-methylpyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

5-bromo-4-methylpyridine-2,3-diamine (0.21 g, 1 mmol) was dissolved in a mixture of EtOH—H2O; to this was added aqueous glyoxal 40% (0.2 ml, 4 mmol) and the resulting mixture was refluxed for 1 h. Upon cooling to room temperature, water was then added. The product was separated, filtered and washed with excess water yielded 7-bromo-8-methylpyrido[2,3-b]pyrazine as a sufficiently enough pure material (0.21 g) for the next step.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customThe product was separated
  3. filtrationfiltered
  4. washwashed with excess water

Sources & evidence

ORD record
ord-881d54a7c35d41f48d4970e46546bf5f
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Reaction notes

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