Reaktion #519480

Reaktionsgleichung

cis-3-[4-(benzyloxy)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ammonium formate

→

cis-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol

Ausbeute 99.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through a pad of celite, which
2. 2
   Waschenwas washed with ethanol (500 mL)
3. 3
   SonstigeThe organic layer was removed under reduced pressure
4. 4
   SonstigeThe resulting solid was dried over night under high vacuum

Vorschrift

A solution of cis-3-[4-(benzyloxy)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.500 g, 1.005 mmol) in absolute ethanol (25 mL) was treated with palladium 10 wt. % on activated carbon (0.100 g, 0.201 mmol) and ammonium formate (0.317 g, 5.03 mmol). The reaction mixture was stirred at 80° C. for 2 h; no starting material was seen by thin layer chromatography. The reaction mixture was filtered through a pad of celite, which was washed with ethanol (500 mL). The organic layer was removed under reduced pressure. The resulting solid was dried over night under high vacuum to give 0.406 g (99%) of cis-4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol. 1H NMR (DMSO-d6, 400 MHz) δ 8.204-8.194 (m, 2H), 7.472-7.437 (m, 2H), 6.947-6.912 (m, 2H), 4.791-4.744 (m, 1H), 2.418 (m, 9H), 2.249-2.243 (m, 2H), 2.193 (s, 3H), 2.077-2.050 (m, 2H), 1.688-1.666 (m, 2H), 1.656-1.578 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 3.47 min (99%).

Quelle