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

HRID 1918850Notes

Reaction equation

HRID 1918850 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 3-(5-acetyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one 108d (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 5-bromo-1-methyl-3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one (126a).

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

Sources & evidence

ORD record
ord-c93555021e3e4995b4f3ff3ad5ced9fd
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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