Glyoxal → HCID 59688962, compound
Reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.CO.[C:12](O)(=O)[CH3:13].C(C=O)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[C:4]([N:3]=1)=[N:9][CH:12]=[CH:13][N:8]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 50 mg (0.27 mmol) of 5-bromopyrazine-2,3-diamine in 2 mL of a 10:1 solution of methanol/acetic acid was added 0.046 mL (0.40 mmol) of glyoxal solution (40 wt. % in water) and the resulting solution was stirred at 50° C. for 4 h. The reaction mixture was cooled to ambient temperature, diluted with 10 mL of ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, and saturated aqueous brine (5 mL each). The organic phase was then dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to yield the title compound as a tan crystalline solid which was used without further purification. LC/MS 211.1, 213.1 (M+1, M+3).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- washwashed with saturated aqueous sodium bicarbonate solution, and saturated aqueous brine (5 mL each)
- dry with materialThe organic phase was then dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-29f44c32ee824a9c823d2938e4a53ef9
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884104B2
Reaction notes
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