Water → HCID 69331850, compound

HRID 915063Notes

Reaction equation

HRID 915063 reaction equation
C1(P([C:24]2[CH:29]=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-:31].[K+].[K+].[NH2:36][C:37]1[N:38]=[C:39]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:40]([C:44]2[CH:45]=[CH:46][C:47](=[O:53])[N:48]([CH:50]([CH3:52])[CH3:51])[N:49]=2)=[N:41][C:42]=1Br.O>C(OCCCC)=C.CC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:29]([C:42]1[N:41]=[C:40]([C:44]2[CH:45]=[CH:46][C:47](=[O:53])[N:48]([CH:50]([CH3:52])[CH3:51])[N:49]=2)[C:39]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[N:38][C:37]=1[NH2:36])(=[O:31])[CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69331850HCID 69331850, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 8108Butyl vinyl etherSolvent

Procedure

In the presence of palladium acetate (8.7 mg), 1,3-bis(diphenylphosphino)propane (35.3 mg) and potassium carbonate (215 mg), a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (501 mg) in butyl vinyl ether (1.5 ml) was refluxed for 20 hours. After addition of water, the mixture was extracted with CHCl3 dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-(6-acetyl-5-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (28 mg).

Workup

  1. temperaturewas refluxed for 20 hours
  2. extractionthe mixture was extracted with CHCl3
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give syrup
  6. customThe syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)
  7. customto give a solid
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-258b7c0fc3ce46109165e0e45c0270bb
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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