Ethanol → 5-Bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one

HRID 592623Notes

Reaction equation

HRID 592623 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]2[N:10]=[C:11]([NH:13][C:14]3[C:15](=[O:22])[N:16]([CH3:21])[CH:17]=[C:18]([Br:20])[CH:19]=3)[CH:12]=[C:6]2[CH2:5]1)(=O)C.[OH-].[Na+].C(O)C.C(OCC)(=O)C>O>[Br:20][C:18]1[CH:19]=[C:14]([NH:13][C:11]2[CH:12]=[C:6]3[CH2:5][NH:4][CH2:9][CH2:8][N:7]3[N:10]=2)[C:15](=[O:22])[N:16]([CH3:21])[CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 580440563-(5-acetyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 580437855-Bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL round bottom flask with a magnetic stirrer and reflux condenser was charged with 125g (250 mg, 0.7 mmol), aqueous NaOH (5N, 6 mL), ethanol (6 mL). The mixture stirred at reflux for 30 min. After this time, ethyl acetate (5 mL) and water (5 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organics were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a 91% yield (200 mg) of crude 125h.

Workup

  1. temperatureA 50 mL round bottom flask with a magnetic stirrer and reflux condenser
  2. temperatureat reflux for 30 min
  3. extractionThe separated aqueous layer was extracted with ethyl acetate (2×5 mL)
  4. washThe combined organics were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a 91% yield (200 mg) of crude 125h.

Sources & evidence

ORD record
ord-967a418324154136843501f768fe7db6
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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