Water → HCID 69102783, compound

HRID 2217233Notes

Reaction equation

HRID 2217233 reaction equation
[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[N:4][C:5]([C:14]2[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.B(Br)(Br)Br.CCOC(C)=O.O>ClCCCl.C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 69102358HCID 69102358, compound

Product 1

HCID 69102783HCID 69102783, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-Amino-6-(6-methoxy-3-pyridyl)-5-phenyl-2-pyrazinecarbonitrile (370 mg) was dissolved in 1,2-dichloroethane (37 ml). To the solution was added 1M boron tribromide solution in CH2Cl2 (12.2 ml) The mixture was stirred at 80° C. for 24 hours. The mixture was cooled to 20-25° C., and portioned to EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, and dried over MgSO4. Evaporation of solvent in vacuo gave reddish solid residue. The residue was pulverized with water, to give 3-amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarbonitrile as powder (254 mg).

Workup

  1. temperatureThe mixture was cooled to 20-25° C.
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of solvent in vacuo
  7. customgave reddish solid residue

Sources & evidence

ORD record
ord-af03e3c79cc14b7cafe25786b204e4f7
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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