Potassium Carbonate → HCID 22346839, compound

HRID 897801Notes

Reaction equation

HRID 897801 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>CN(C)C=O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH:24]3[CH2:29][CH2:28][N:27]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:26][CH2:25]3)[N:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)[C:22]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 223472623-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 22346839HCID 22346839, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-phenoxyphenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.10 g, 0.00026 mol, 1 eq.) and potassium carbonate (0.072 g, 0.000526 mol, 2 eq.) in anhydrous N,N-dimethylformamide (8 mL) was added tert-butyl 2-bromoacetate (0.0768 g, 0.00039 mol, 1.5 eq.) at room temperature. The mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and washed with water (3 mL). The solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane (5:95) as mobile phase to yield tert-butyl 2-{4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidino}acetate (0.10 g, 0.0002 mol).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  3. washwashed with water (3 mL)
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3b1b1ad6804b495085d766735b085aa6
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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