Reaktion #304294

Reaktionsgleichung

3-(Bromomethyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one

3-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

potassium tert-butoxide

→

desired product

3-((4-amino-3-(3-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one

3-((4-amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one

Ausbeute 139.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred at RT for 30 min
2. 2
   Extraktionextracted with ethyl acetate (3×50 mL)
3. 3
   WaschenThe combined organic layer was washed with brine (25 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   Sonstigethe residue was purified by flash column chromatography on silica gel (2-20% MeOH/DCM)

Vorschrift

3-(3-Methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1701)(964 mg, 4 mmol) and potassium tert-butoxide (0.44 g, 4 mmol) were dissolved in anhydrous DMF (150 mL) and stirred at RT for 30 min. 3-(Bromomethyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (1610) (1.37 g, 4.0 mmol) was added. The resulting mixture was stirred at RT for 30 min, poured into ice water (30 mL) and then extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (25 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (2-20% MeOH/DCM) to afford the desired product, 3-((4-amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (1702) (1.4 g, 70% yield) as a white solid.

Quelle