Water → HCID 69103834, compound

HRID 2217256Notes

Reaction equation

HRID 2217256 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[O-].[Na+].C[CH2:29][O:30]C(C)=O.O>CN1C(=O)CCC1.[Cu]I>[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[O:30][CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 11429076HCID 11429076, compound

Product 1

HCID 69103834HCID 69103834, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg), sodium methoxide (70 mg), CuI (5 mg) in NMP (1.0 ml) was heated at 100° C. for 2.5 hours. After cooling, EtOAc and water 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 recrystallized from MeOH-IPE to give 5-(5-amino-6-methoxy-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (58 mg).

Workup

  1. temperatureAfter cooling
  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 recrystallized from MeOH-IPE

Sources & evidence

ORD record
ord-459ddf0ba64044ee93fd555317af3a8c
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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