Methyl iodide → 5-Bromo-3-(5-ethyl-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 407675Notes

Reaction equation

HRID 407675 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][CH3:17])[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[H-].[Na+].I[CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH2:16][CH3:17])[N:13]([CH3:21])[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 670161795-Bromo-3-(5-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

Product 1

HCID 866839595-Bromo-3-(5-ethyl-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 122a (598 mg, 2.0 mmol) in DMF (10 mL) was added NaH (64 mg, 1.6 mmol) at 0° C. and the mixture was stirred for 0.5 h. To the mixture was added iodomethane (227 mg, 1.6 mmol) in DMF dropwise at 0° C. The mixture was stirred for 0.5 h and quenched with water (20 mL). It was then extracted with dichloromethane (3×30 mL). The combined extract was concentrated under reduced pressure and the residue was purified with silica-gel column chromatography eluting with petroleum ether/ethyl acetate (5:1 to 2:1) to afford 122b (360 mg, 58%) as a light yellow solid. MS-ESI: [M+H]+ 311.1

Workup

  1. stirringThe mixture was stirred for 0.5 h
  2. customquenched with water (20 mL)
  3. extractionIt was then extracted with dichloromethane (3×30 mL)
  4. extractionThe combined extract
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified with silica-gel column chromatography
  7. washeluting with petroleum ether/ethyl acetate (5:1 to 2:1)

Sources & evidence

ORD record
ord-563a34f3f76e41c39c02ae8649a8060c
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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