2-Amino-3-chloropyrazine → 8-Chloro-2-ethylimidazo[1,2-a]pyrazine-3-carboxylic Acid Methyl Ester

HRID 500984Notes

Reaction equation

HRID 500984 reaction equation
[Cl:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.Cl[CH:10]([C:15](=O)[CH2:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12]>>[CH3:14][O:13][C:11]([C:10]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]2=[N:8][C:15]=1[CH2:16][CH3:17])=[O:12]

Participants

3

Reactant 2

HCID 2762242-Amino-3-chloropyrazineHCID 545096Methyl 2-chloro-3-oxopentanoate

Product 1

HCID 865920598-Chloro-2-ethylimidazo[1,2-a]pyrazine-3-carboxylic Acid Methyl EsterYield 25.5%

Conditions

Temperature
170 °C

Procedure

3-Chloro-2-aminopyrazine (2.1 g, 16.2 mmol) and methyl 2-chloro-3-oxopentanoate (6.7 mL, 48.6 mmol) were mixed, and heated under stirring at 170° C. for 2 hours. After being allowed to cool, the unnecessary materials were filtered off and washed with ethyl acetate, and then filtrates were combined and evaporated. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (0.99 g) as white crystals.

Workup

  1. temperatureheated
  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=4:1)

Sources & evidence

ORD record
ord-0f335c3285944e60bac9473f38c4b92d
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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