Methyl iodide → HCID 69103001, compound

HRID 2217249Notes

Reaction equation

HRID 2217249 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]([C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=2)=[N:8][C:9]=1[CH2:10][OH:11].CI.[CH3:30]COC(C)=O>CN(C=O)C.O>[NH2:3][C:4]1[N:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]([C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=2)=[N:8][C:9]=1[CH2:10][O:11][CH3:30]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 44216363HCID 44216363, compound

Product 1

HCID 69103001HCID 69103001, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Under ice-bath cooling, NaH (60% pure, 18 mg) was added to a suspension of 5-[5-amino-6-(hydroxymethyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (100 mg) in DMF (1.0 ml). After 10 minute stirring, MeI (127 mg) was added to the mixture. After 10 minutes stirring at the same temperature, the mixture was allowed to warm to 25° C. After 3.5 hours stirring, 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 and the residue was purified by column chromatography, triturated with IPE, and dried in vacuo to give 5-[5-amino-6-(methoxymethyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (40 mg).

Workup

  1. temperatureUnder ice-bath cooling
  2. stirringAfter 10 minutes stirring at the same temperature
  3. stirringAfter 3.5 hours stirring
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography
  9. customtriturated with IPE
  10. customdried in vacuo

Sources & evidence

ORD record
ord-03d0f527e61f4651a0d3239fd28234c1
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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