Water → 6-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone

HRID 915053

Reaction equation

HRID 915053 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]([Si:34]([CH3:37])([CH3:36])[CH3:35])#[CH:33].O>ClCCCl.[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][Si:34]([CH3:37])([CH3:36])[CH3:35]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 693319796-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone

Reagents, catalysts & solvents 3

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

Conditions

Temperature
27.5 °C

Procedure

In the presence of copper(I) iodide (25 mg) and dichlorobis(triphenylphosphine)palladium(II) (91 mg), triethylamine (0.397 ml) was dropwise added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (1.00 g) and ethynyl(trimethyl)silane (0.716 ml) in 1,2-dichloroethane (20 ml) under ice-cooling. The mixture was stirred at same temperature for one hour and at 25-30° C. for 18 hours. After addition of water, an organic layer was collected, washed with sat. aq. sodium chloride, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (80:20 v/v) to give a solid. The solid was crystallized from a mixture of acetone and n-hexane to give 6-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone (431 mg).

Workup

  1. temperaturecooling
  2. customan organic layer was collected
  3. washwashed with sat. aq. sodium chloride
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (80:20 v/v)
  8. customto give a solid
  9. customThe solid was crystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-e0d9c52089e841829f92c01da3232bd9
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Linked notes

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