Toluene → 2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl) amino]carbonothioyl}acetamide

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 4-[1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-phenylamine (0.199 g, 0.63 mmol, 1.0 eq.), toluene (10 ml), ethanol (10 ml) and phenyl-acetyl isothiocyanate (0.33 g, 2.0 mmol, 3.0 eq). The reaction mixture was stirred at room temperature overnight. After removal of solvent in vacuo, the product was separated by flash chromatography using a 3:1 hexane/ethyl acetate solution as the eluent to give 2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)amino]carbonothioyl}acetamide (0.17 g, 54% yield). 1H NMR (400 MHz, DMSO): 12.39 (s, 1H), 11.78 (s, 1H), 8.59 (s, 1H), 8.20 (s, 1H), 7.71 (d, 2H), 7.53 (t, 1H), 7.34 (m, 5H), 7.26 (m, 1H), 5.97 (d, 1H), 3.94 (d, 1H), 3.73 (s, 2H), 3.72 (m 1H), 3.40 (s, 2H), 2.05 (m, 1H), 1.93 (m, 1H), 1.77 (m, 1H), 1.58 (m, 1H); MS (ESI) for C25H24N6O3S: 489 (MH+).

Provenance & Evidence