Reaktion #70884

Reaktionsgleichung

NaOH

NaNO2

3-amino-6-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine

3-Amino-6-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine

H3PO2

→

title compound

Ausbeute 42.0%

6-(4-Fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine

Ausbeute 42.0%

Lösungsmittel

water

AcOH

water

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGIt was stirred at 0° C. for 6 h
2. 2
   Temperaturto cool to room temperature
3. 3
   Extraktionwas extracted with EtOAc
4. 4
   TrocknenThe combined organic phases were dried over Na2SO4
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigeThe crude product obtained
7. 7
   Sonstigewas purified by chromatography on silica gel
8. 8
   Temperaturof increasing polarity as eluent

Vorschrift

To a solution of 3-amino-6-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridine (10.00 g, 28.4 mmol, obtained in example 180) in AcOH (52 mL), water (22 mL) and HCl conc. (5.7 mL), cooled to 0° C., a solution of NaNO2 (2.30 g, 33.4 mmol) in water (7.5 mL) was added dropwise. It was stirred for 30 min at 0° C., and H3PO2 (50% aqueous solution, 56.8 mL) was added slowly. It was stirred at 0° C. for 6 h. It was allowed to cool to room temperature, basified at 0° C. by slow addition of 6 N NaOH hasta pH=8 and was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 4.00 g of the title compound (yield: 42%)

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