Chloroacetaldehyde → Imidazo(1,2-a)pyrazine

HRID 1013740Notes

Reaction equation

HRID 1013740 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]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 78747Aminopyrazine

Product 1

HCID 2771670Imidazo(1,2-a)pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperaturewith reflux condenser
  2. temperatureheated
  3. temperatureunder reflux overnight
  4. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4bf59c1728684b9c8a5a313d1ca6f0d8
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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