Potassium Carbonate → 4-Amino-1-[1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidine-3-carbonitrile

HRID 522327Notes

Reaction equation

HRID 522327 reaction equation
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[NH2:23][C:24]1[N:29]=[CH:28][N:27]=[C:26]2[NH:30][N:31]=[C:32]([C:33]#[N:34])[C:25]=12.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:23][C:24]1[N:29]=[CH:28][N:27]=[C:26]2[N:30]([CH:2]3[CH2:6][CH2:5][N:4]([C:7]4[CH:8]=[N:9][N:10]([C:15]5[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=5)[C:11]=4[CH:12]([CH3:14])[CH3:13])[C:3]3=[O:22])[N:31]=[C:32]([C:33]#[N:34])[C:25]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 867230343-Bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-oneHCID 178510695HCID 178510695, compound

Product 1

HCID 867230414-Amino-1-[1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidine-3-carbonitrileYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.055 g, 0.15 mmol), 4-amino-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile (0.050 g, 0.31 mmol) and K2CO3 (0.050 g, 0.36 mmol) in DMF (2.0 mL) was stirred at 60° C. for 1 hr. The mixture was then cooled to room temperature, quenched with water (30 mL), and extracted with IPA:CHCl3 (1:2 v/v, 100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, 0˜10% MeOH/EtOAc gradient elution) to give 4-amino-1-[1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-d]pyrimidine-3-carbonitrile (0.055 g, 82%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with water (30 mL)
  3. extractionextracted with IPA:CHCl3 (1:2 v/v, 100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (SiO2, 0˜10% MeOH/EtOAc gradient elution)

Sources & evidence

ORD record
ord-929c3f717c8f4c5992a8e254a1f54b6c
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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