Reaktion #304295

Reaktionsgleichung

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

BBr3

→

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

Ausbeute 91.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to RT
2. 2
   Extraktionextracted with ethyl acetate (3×50 mL)
3. 3
   WaschenThe combined organic layer was washed with brine (20 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 (10-50% MeOH/CH2Cl2)

Vorschrift

To a solution of 3-((4-amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one (1702)(100 mg, 0.2 mmol) in CH2Cl2 (20 mL) at −78° C. under a nitrogen atmosphere, BBr3 (1 mL) was added and the resulting mixture was stirred at −78° C. for 3 h. The mixture was allowed to warm to RT, poured into ice-water (200 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (10-50% MeOH/CH2Cl2) to afford the 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 (1613)(87 mg, 91% yield) as a white solid.

Quelle