Chloroacetaldehyde → Imidazo[1,2-a]pyrazine-6-carbonitrile

HRID 1890579Notes

Reaction equation

HRID 1890579 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.Cl[CH2:11][CH:12]=O>C(O)C>[N:1]1[CH:11]=[CH:12][N:3]2[CH:4]=[C:5]([C:8]#[N:9])[N:6]=[CH:7][C:2]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 139252945-Aminopyrazine-2-carbonitrile

Product 1

HCID 67305172Imidazo[1,2-a]pyrazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-aminopyrazine-2-carbonitrile (5-1) (350 mg, 2.92 mmol) in ethanol (15 mL) was added 2-chloroacetaldehyde (4 mL, 40% in water). The mixture was stirred at 110° C. overnight. The solution was concentrated, then purified by chromatography on silica gel to afford the title compound (280 mg). MS (m/z): 145.1 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-295bf6c8970d49e9b172c1d7b4254545
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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