Chloroacetaldehyde → Imidazo(1,2-a)pyrazine
Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].Cl[CH2:9][CH:10]=O>CCO>[N:7]1[CH:9]=[CH:10][N:1]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A round bottom set up with reflux condenser was charged with pyrazin-2-amine (1000 mg, 10.52 mmol), 2-chloroacetaldehyde (˜50% wt) (2.03 ml, 31.55 mmol), and EtOH (23 mL) and heated under reflux overnight. Next day LC/MS showed completion. The mixture was concentrated and passed through a plug of silica (solvent used: 1% MeOH/DCM) to afford imidazo[1,2-a]pyrazine as off-white solid. MS [M+H]=120.1; Calc'd for C6H5N3: 119.1
Workup
- temperaturewith reflux condenser
- temperatureheated
- temperatureunder reflux overnight
- concentrationThe mixture was concentrated
Sources & evidence
- ORD record
- ord-9ca6e5ea8c1940f6b09438655bf32812
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776857B2
Reaction notes
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