Triphenylphosphine → N1-[4-(4-amino-1 tetrahydro-2H-4-pyranyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide

Diethyl azodicarboxylate (0.07 mL, 0.45 mmol) was added into a mixture of N1-[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.10 g, 0.22 mmol), triphenylphosphine (0.12 g, 0.45 mmol) and tetrahydro-4H-pyran-4-ol (0.04 g, 0.34 mmol) in tetrahydrofuran (5 mL) and the mixture was stirred at ambient temperature overnight. Tetrahydro-4H-pyran-4-ol (0.01 g, 0.11 mmol), triphenylphosphine (0.04 g, 0.15 mmol) and diethyl azodicarboxylate (0.02 mL, 0.15 mmol) were added and the mixture was stirred at ambient temperature for 5 hours. The solvents were evaporated and the residue was purified by preparative HPLC to yield N1-[4-(4-amino-1-tetrahydro-2H-4-pyranyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.03 g, 0.06 mmol) as a white solid: 1H NMR (DMSO-d6 400 MHz) (9.91 (dd, 1H), 8.30(d, 1H), 8.25 (s, 1H), 8.00 (t, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.34 (s, 1H), 7.31 (d, 1H), 6.90 (br, 2H), 4.95 (m, 1H), 4.02 (m, 2H), 3.95 (s, 3H), 3.56 (t, 2H), 2.22 (m, 2H), 1.89 (m, 2H);

1. stirringthe mixture was stirred at ambient temperature for 5 hours
2. customThe solvents were evaporated
3. customthe residue was purified by preparative HPLC

ORD-Eintrag

ord-a847397345c247ca86e9a6ad527a99b8

Quelldatensatz

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06921763B2