Isopropyl iodide → HCID 69104332, compound

HRID 2217232Notes

Reaction equation

HRID 2217232 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([OH:23])=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[CH:24](I)([CH3:26])[CH3:25].CC([O-])(C)C.[K+].CCOC(C)=O>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 69102420HCID 69102420, compound

Product 1

HCID 69104332HCID 69104332, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

3-Amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (283 mg) was dissolved in DMF (10 ml). To the solution were added i-PrI (172 mg) and t-BuOK (114 mg). The mixture was stirred at 20-30° C. for 2 hours. The reaction mixture was portioned EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic solution was washed with brine and dried over MgSO4. Evaporation of solvent gave oily residue. The above residue was purified by chromatography on silica gel (EtOAc only-EtOAc:MeOH=96:4, v/v) to give isopropyl 3-amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylate as yellow crystal (64 mg).

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave oily residue
  7. customThe above residue was purified by chromatography on silica gel (EtOAc only-EtOAc

Sources & evidence

ORD record
ord-12fed4cfd29546e3ba76929a9a169a45
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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