Sodium hydride → HCID 57964880, compound

HRID 1931781Notes

Reaction equation

HRID 1931781 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:31]3=[N:32][C:33]([O:37][CH3:38])=[N:34][C:35](Cl)=[C:30]3[CH:29]=[N:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>CN(C)C=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:31]3=[N:32][C:33]([O:37][CH3:38])=[N:34][C:35]([O:13][C:10]4[CH:11]=[CH:12][C:7]([S:4]([CH3:3])(=[O:5])=[O:6])=[CH:8][CH:9]=4)=[C:30]3[CH:29]=[N:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1233504-(Methylsulfonyl)phenolHCID 86636111HCID 86636111, compound

Product 1

HCID 57964880HCID 57964880, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil; 2 mmol) is added to a solution of 4-(methylsulfonyl)phenol (1.6 mmol) in dimethylformamide (9 mL) and the mixture is stirred at room temperature for 20 min. A solution of crude 4-(4-chloro-6-methoxy-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1 mmol) in dimethylformamide (5 mL) is added. The reaction mixture is heated at 50° C. for 8 h. Saturated aqueous ammonium chloride solution is added and the mixture is extracted three times with ethyl acetate. The organic layer is washed with water and brine, dried (magnesium sulfate), filtered, evaporated and purified by flash chromatography on silica gel to give 4-[4-(4-methanesulfonyl-phenoxy)-6-methoxy-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe reaction mixture is heated at 50° C. for 8 h
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-016df30ea3724e1a986fc8a34a2ea5df
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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