Sodium Carbonate → 4-[4-(4-Methanesulfinyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1931665

Reaktionsgleichung

Reaktionsgleichung von HRID 1931665
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:3].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:28]3=[N:29][CH:30]=[N:31][C:32](Cl)=[C:27]3[CH:26]=[N:25]2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([N:24]2[C:28]3=[N:29][CH:30]=[N:31][C:32]([O:10][C:7]4[CH:8]=[CH:9][C:4]([S:2]([CH3:1])=[O:3])=[CH:5][CH:6]=4)=[C:27]3[CH:26]=[N:25]2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 1519364-(Methylsulfinyl)phenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Produkt 1

HCID 579650044-[4-(4-Methanesulfinyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl esterAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 4-methanesulfinyl-phenol (Combi-Blocks Inc, San Diego, Calif., USA; 14 mg, 0.089 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 30 mg, 0.089 mmol), and potassium carbonate (27 mg, 0.196 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to give 4-[4-(4-methanesulfinyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (15 mg, 36%) as a white solid. Mass spectrum MH+=458.

Aufarbeitung

  1. filtrationthe mixture was then filtered through a pad of silica gel
  2. customto remove the precipitate
  3. washThe silica gel pad was washed with methanol
  4. customthe solvents were evaporated from the filtrate
  5. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2dbadfeed229409f86919153a4f283f7
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188098B2

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