Cesium carbonate → HCID 86603760, compound

HRID 2376153Notes

Reaction equation

HRID 2376153 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:48]1[CH:53]=[N:52][CH:51]=[C:50]([Cl:54])[N:49]=1.[CH2:55]([N:62]1[CH2:66][CH2:65][C@@H:64]([NH2:67])[CH2:63]1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:55]([N:62]1[CH2:66][CH2:65][C@@H:64]([NH:67][C:48]2[CH:53]=[N:52][CH:51]=[C:50]([Cl:54])[N:49]=2)[CH2:63]1)[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 785042,6-DichloropyrazineHCID 634876Binap, (A+-)-HCID 1519354(3R)-1-benzylpyrrolidin-3-amine

Product 1

HCID 86603760HCID 86603760, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Palladium(II) acetate (75 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (313 mg) in dioxane (5 mL) was stirred at ambient temperature for 15 minutes. To this suspension was added 2,6-dichloropyrazine (1.00 g), (3R)-(−)-1-benzyl-3-aminopyrrolidine (1.42 g), and cesium carbonate (3.28 g), and the mixture was heated at 80 C for 8 hours. The resulting mixture was allowed to cool to ambient temperature, poured into water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform/methanol=96/4 v/v) to give N-[(3R)-1-benzyl-3-pyrrolidinyl]-6-chloro-2-pyrazinamine (1.00 g) as a yellow solid.

Workup

  1. temperaturethe mixture was heated at 80 C for 8 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=96/4 v/v)

Sources & evidence

ORD record
ord-9ec612ac1fa246e28a37ac17483be619
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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