(Diethylamino)sulfur trifluoride → HCID 25213477, compound

Participants

Reaction Steps

To a solution of 3-[(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-hydroxy-methyl]-5-methyl-benzonitrile (100) (55.7 mg, 0.17 mmol) in dichloromethane (2.0 mL) at 0° C. was added (diethylamino)sulfur trifluoride (33 μL, 0.255 mmol) and reaction mixture stirred for 1 h. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethyl acetate (2×). The combined organic layer was dried (MgSO4), concentrated and purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O) to give a white powder after lyophilization (45 mg, 80%). 1H NMR (300 MHz, CD3OD): 7.60 (s, 1H), 7.55 (s, 1H), 7.46 (s, 1H), 7.04 (d, J=45.9 Hz, 1H), 3.75-3.57 (m, 2H), 2.94-2.89 (m, 1H), 2.40 (s, 3H), 1.24 (d, J=6.9 Hz, 3H), 1.1-1.0 (s, 6H); %). 19F NMR (CD3OD): −180.5; Mass Spectrum: 330.1 (M+H).

Provenance & Evidence