Phenol → HCID 57964899, compound

HRID 1931623Notes

Reaction equation

HRID 1931623 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:27]3=[N:28][CH:29]=[N:30][C:31](Cl)=[C:26]3[CH:25]=[N:24]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([N:23]2[C:27]3=[N:28][CH:29]=[N:30][C:31]([O:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)=[C:26]3[CH:25]=[N:24]2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964899HCID 57964899, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride [60% dispersion in paraffin; 1.5 equivalents] in DMF was added to a solution of phenol (1 equivalent) in dimethylformamide (0.2 M) at 0° C. under nitrogen. After 30 minutes, 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 1 equivalent) was added and the mixture was stirred for 12 h at room temperature. Saturated aqueous ammonium chloride was added and the solution was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate), filtered, evaporated, and purified by chromatography on neutral alumina, eluting with ethyl acetate/hexane, to give 4-(4-phenoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by chromatography on neutral alumina
  6. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-4c8acc701c384721b15e477e30df6e13
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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