2-Amino-3-chloropyrazine → HCID 86670917, compound

HRID 1186491Notes

Reaction equation

HRID 1186491 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](Br)[CH:9](OC)OC)[N:3]=1.[Cl:15][C:16]1[C:17]([NH2:22])=[N:18][CH:19]=[CH:20][N:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC#N.O>[Br:1][C:2]1[N:3]=[C:4]([C:8]2[N:18]3[CH:19]=[CH:20][N:21]=[C:16]([Cl:15])[C:17]3=[N:22][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2762242-Amino-3-chloropyrazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 866709182-Bromo-6-(1-bromo-2,2-dimethoxy-ethyl)-pyridine

Product 1

HCID 86670917HCID 86670917, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-6-(1-bromo-2,2-dimethoxy-ethyl)-pyridine (from Example 37 supra) (5.267 g, 16.2 mmol), 3-chloropyrazin-2-amine (2.1 g, 16.2 mmol), and pTsOH.H2O (2.1 g, 11 mmol) in CH3CN (900 mL) and water (90 mL) was stirred and heated at reflux overnight. The reaction mixture was then cooled to room temperature, concentrated under reduced pressure. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine. (Yield 4.86 g, 52%). LC-MS: [M+H]+ 309.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1)

Sources & evidence

ORD record
ord-3de223f2cfda423bb3228e612169f1f8
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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