Methyl 2-chloro-3-oxopentanoate → 8-Bromo-2-ethyl-6-methylimidazo[1,2-a]pyrazine-3-carboxylic Acid Methyl Ester

HRID 500986Notes

Reaction equation

HRID 500986 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.Cl[CH:11]([C:16](=O)[CH2:17][CH3:18])[C:12]([O:14][CH3:15])=[O:13]>>[CH3:15][O:14][C:12]([C:11]1[N:4]2[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([Br:1])[C:3]2=[N:9][C:16]=1[CH2:17][CH3:18])=[O:13]

Participants

3

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 98990432-Amino-3-bromo-5-methylpyrazine

Product 1

HCID 865920608-Bromo-2-ethyl-6-methylimidazo[1,2-a]pyrazine-3-carboxylic Acid Methyl EsterYield 5.8%

Conditions

Temperature
130 °C

Procedure

3-Bromo-5-methyl-2-pyrazineamine (3.5 g, 18.6 mmol) and methyl 2-chloro-3-oxopentanoate (6.7 mL, 48.6 mmol) were mixed, and the mixture was heated under stirring at 130° C. for 1 hour. After being allowed to cool, the unnecessary materials were filtered off and washed with ethyl acetate, and then the filtrates were combined and evaporated. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give the title compound (0.32 g) as pale yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. filtrationthe unnecessary materials were filtered off
  4. washwashed with ethyl acetate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-db47049d488046d3988a14e3a330500c
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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