Triethylamine → HCID 178429489, compound

Participants

Reaction Steps

A mixture of 3-(bromomethyl)-4-chloroquinoline (982 mg, 3.8 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (450 mg, 3.2 mmol), and triethylamine (1.3 mL, 9.5 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The solvent was evaporated to dryness and co-evaporated with EtOAc (20 mL). The product was suspended in water (200 mL). The product was recovered by filtration and washed with water (3×200 mL), diethyl ether (1×50 mL), and hexanes (2×50 mL). The solid material was dried in vacuo, affording the title compound (951 mg, 79% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.65 (s, 2H), 6.02 (s (br), 1H), 7.75 (td, 1H, J=1.4 Hz, 6.8 Hz), 7.83 (td, 1H, J=1.4 Hz, 6.8 Hz), 8.05 (dd, 1H, J=0.6 Hz, 7.6 Hz), 8.20 (dd, 1H, J=0.6 Hz, 8.4 Hz), 9.10 (s, 1H); M+ 318.

Provenance & Evidence