Lithium Hydroxide → HCID 136352699, compound

HRID 383562Notes

Reaction equation

HRID 383562 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2=[N:14][C:15]([OH:23])=[C:16](C(OCC)=O)[N:17]=[C:12]2[CH:11]=[N:10]1.[OH-].[Li+].C1C(=O)N([Br:33])C(=O)C1>O.CC#N>[Br:33][C:16]1[C:15](=[O:23])[NH:14][C:13]2[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[N:10]=[CH:11][C:12]=2[N:17]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 67184N-bromobutanimideHCID 178470166HCID 178470166, compound

Product 1

HCID 136352699HCID 136352699, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl 1-(2,6-difluorophenyl)-6-hydroxy-1H-pyrazolo[3,4-b]pyrazine-5-carboxylate (1.27 g, 3.70 mmol) in 2.5 mL of water and 2.5 mL of CH3CN at RT was added lithium hydroxide (209 mg, 8.72 mmol), and the resulting mixture was warmed to 60° C. for 0.5 h. The reaction mixture was cooled with an ice bath, and NBS (1059 mg, 5.95 mmol) was added in small portions. The reaction mixture was stirred at RT for 0.5 h, then partitioned between a saturated solution of NaHCO3 and EtOAc. The EtOAc layer was washed with brine, dried over MgSO4, filtered and concentrated to afford 5-bromo-1-(2,6-difluorophenyl)-1H-pyrazolo[4,3-b]pyrazin-6(7H)-one (1210 mg, 93.3% yield) a a brown amorphous solid. This crude material was used without further purification. MS (ES+): 327.0/329.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled with an ice bath
  2. custompartitioned between a saturated solution of NaHCO3 and EtOAc
  3. washThe EtOAc layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95e6f78ebff74c7f974840f9da8e10d3
Source dataset
uspto-grants-2013_02
Patent number
US08367671B2

Reaction notes

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