Dimethylformamide → HCID 46842454, compound

Participants

Reaction Conditions

Reaction Steps

Propargyl alcohol (0.045 mL, 0.76 mmol) and PdCl2(PPh3)2 (0.007 g, 0.01 mmol) were added to a solution of N-(4-(3-(4-sec-butylphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2-iodophenyl)-2,2,2-trifluoroacetamide (0.300 g, 0.51 mmol) in TEA (10 mL) and DMF (3 mL). After heating to 60° C. for 5 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 80% EtOAc in heptane, plus further purification by flash chromatography on silica gel, eluting with 10% to 50% EtOAc in CH2Cl2, afforded the title compound as a white solid (0.065 g, 29%). 1H-NMR (300 MHz, DMSO-d6): δ11.09 (s, 1H), 8.18 (d, J=7.1 Hz, 1H), 7.87-7.90 (m, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.47-7.64 (m, 2H), 6.93-7.25 (m, 6H), 6.19 (s, 1H), 5.23 (t, J=5.6 Hz, 1H), 4.54 (d, J=5.5 Hz, 2H), 2.53-2.61 (m, 1H), 1.30-1.62 (m, 2H), 1.12 (d, J=6.9 Hz, 3H), 0.63 (t, J=7.2 Hz, 3H). MS (APCI) m/z: 424 (M+H)+.

Provenance & Evidence