Water → 6-[5-amino-3-phenyl-6-(2-pyridylethynyl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone

HRID 915055Notes

Reaction equation

HRID 915055 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1Br.[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)#[CH:33].O>ClCCCl.CC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1[C:33]#[C:32][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 137268EthynylpyridineHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 693319246-[5-amino-3-phenyl-6-(2-pyridylethynyl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 111,2-DichloroethaneSolventHCID 180AcetoneSolvent

Procedure

In the presence of copper(I) iodide (3.7 mg) and dichlorobis(triphenylphosphine)palladium(II) (13.7 mg), triethylamine (0.0596 ml) was dropwise added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and 2-ethynylpyridine (0.0431 ml) in 1,2-dichloroethane (1.5 ml) at 30-35° C. The mixture was stirred at the same temperature for 18 hours. Water was added to the reaction mixture to give a solid. The solid was purified by column chromatography on silica gel (EtOAc only) to give a solid. The solid was suspended in acetone to give 6-[5-amino-3-phenyl-6-(2-pyridylethynyl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (88 mg).

Workup

  1. customto give a solid
  2. customThe solid was purified by column chromatography on silica gel (EtOAc only)
  3. customto give a solid

Sources & evidence

ORD record
ord-17aff9ee6fb54284ba25c312070c6593
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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