Potassium Carbonate → 2-Chloro-3-(2-phenoxyethylamino)pyrazine

HRID 991624Notes

Reaction equation

HRID 991624 reaction equation
[O:1]([CH2:8][CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:11][C:12]1[C:17](Cl)=[N:16][CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOCC>[Cl:11][C:12]1[C:17]([NH:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 156512-PhenoxyethanamineHCID 785752,3-Dichloropyrazine

Product 1

HCID 220364242-Chloro-3-(2-phenoxyethylamino)pyrazineYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-phenoxyethylamine (2.65 g, 19.3 mmol), 2,3-dichloropyrazine (2.88 g, 19.3 mmol) and K2CO3 (2.67 g, 19.3 mmol) in acetonitrile (8 mL) was stirred in a sealed tube for 12 h at room temperature, and for a further 9.5 h at 80° C. The reaction mixture was diluted with ether, filtered, and concentrated. The residue was purified by chromatography on silica gel using n-hexane/EtOAc (7:3) as eluent to give 2.36 g (49%) of the title compound as a yellowish oil that solidified on standing: mp 51-53° C.; HRMS m/z calcd for C12H12ClN30 (M)+ 249.0669, found 249.0659. Anal. (Cl2H12ClN30) C, H, N.

Workup

  1. waitfor a further 9.5 h at 80° C
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1aa95db4fcd840e3bf23534af97d1cd0
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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