Hydrochloric Acid → Ethyl 2-methylimidazo[1,2-a]pyrazine-3-carboxylate

HRID 1172961Notes

Reaction equation

HRID 1172961 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].Cl[CH:9]([C:15](=O)[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl>C(O)C.CCOCC>[CH2:13]([O:12][C:10]([C:9]1[N:1]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]2=[N:7][C:15]=1[CH3:16])=[O:11])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 78747Aminopyrazine

Product 1

HCID 13416932Ethyl 2-methylimidazo[1,2-a]pyrazine-3-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of pyrazin-2-amine (3.6 g, 37.9 mmol) and ethyl 2-chloro-3-oxobutanoate (5.24 ml, 37.9 mmol) in ethanol (30 ml) was heated at reflux for 9 hours. A 1N solution of HCl in ether was added and the mixture was concentrated under reduced pressure. The residue was triturated with 3×50 ml acetonitrile and filtered to yield crude 2-Methyl-imidazo[1,2-a]pyrazine-3-carboxylic acid ethyl ester (4.5 g, 58%) as an amorphous solid which was used in the next step without further purification.

Workup

  1. temperatureat reflux for 9 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was triturated with 3×50 ml acetonitrile
  4. filtrationfiltered

Sources & evidence

ORD record
ord-38fd8b93339a4a6890cf9408bb2d2fb8
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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