Water → HCID 69103739, compound

HRID 2217243Notes

Reaction equation

HRID 2217243 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[C:10]([C:26]([NH2:28])=[O:27])=[N:11][C:12]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH:23]([CH3:25])[CH3:24])[CH:17]=2)=[C:13](Cl)[N:14]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[NH2:8][C:9]1[C:10]([C:26]([NH2:28])=[O:27])=[N:11][C:12]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH:23]([CH3:25])[CH3:24])[CH:17]=2)=[C:13]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[N:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6077842-(Tributylstannyl)pyridineHCID 86598204HCID 86598204, compound

Product 1

HCID 69103739HCID 69103739, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A toluene solution of 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide (200 mg), 2-(tributylstannyl)pyridine (311 mg), and Pd(PPh3)4 (22.5 mg) was refluxed for 5 hours. Water (20 ml) and EtOAc (15 ml) were poured into the reaction mixture and the aqueous solution was extracted with EtOAc. The organic layer was washed with water and brine, and dried over MgSO4. After filtration, the solvent was removed under reduced pressure. The residual solid was placed on a column of silica-gel and eluted with CHCl3—MeOH (97:3). The eluent was evaporated and the residue was suspended with IPE and filtrated to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-(2-pyridyl)-2-pyrazinecarboxamide (64 mg) as a yellow powder.

Workup

  1. extractionthe aqueous solution was extracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. customthe solvent was removed under reduced pressure
  6. washeluted with CHCl3—MeOH (97:3)
  7. customThe eluent was evaporated
  8. filtrationfiltrated

Sources & evidence

ORD record
ord-6e6702b96c0f4877b4bcf83d0a90f21d
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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