Water → HCID 86598208, compound

HRID 2217255Notes

Reaction equation

HRID 2217255 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]([C:14]2[CH:15]=[CH:16][C:17](=[O:23])[N:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=2)=[N:6][C:7]=1[C:8]#[C:9][Si](C)(C)C.C([O-])([O-])=O.[K+].[K+].O.CCOC(C)=O>CO>[NH2:1][C:2]1[N:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]([C:14]2[CH:15]=[CH:16][C:17](=[O:23])[N:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=2)=[N:6][C:7]=1[C:8]#[CH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69103390HCID 69103390, compound

Product 1

HCID 86598208HCID 86598208, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-1-isopropyl-2(1H)-pyridone (300 mg) and sat. K2CO3 in MeOH (4.5 ml) was stirred at 25° C. for 3 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 short column (silica-gel; CH2Cl2) and recrystallized from EtOH to give 5-(5-amino-6-ethynyl-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg).

Workup

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

Sources & evidence

ORD record
ord-e7304bafd9dc40f08cabe2ff1347945f
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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