Dichloromethane → HCID 69103390, compound

HRID 2217254Notes

Reaction equation

HRID 2217254 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])#[CH:26].C(Cl)Cl.CCN(CC)CC>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.[Cu]I.CCOC(C)=O.O>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1[C:26]#[C:25][Si:27]([CH3:30])([CH3:29])[CH3:28]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11429076HCID 11429076, compound

Product 1

HCID 69103390HCID 69103390, compoundYield 71.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (500 mg), ethynyl(trimethyl)silane (255 mg), PdCl2(PPh3)2 (46 mg), CuI (12 mg), and CH2Cl2 (10 ml), was added NEt3 (0.2 ml) under ice-bath cooling. The mixture was allowed to warm to 25° C. and stirred for 15 hours. Water and EtOAc were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH), recrystallized from EtOH, and dried in vacuo to give 5-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-1-isopropyl-2(1H)-pyridone (373 mg).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH)
  7. customrecrystallized from EtOH
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3d6bc959d90647bd96d831f161d486d0
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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