2,4-Dichloro-1,3,5-triazine → HCID 22496132, compound

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-1,3,5-triazine (1.95 g, 13 mmol) was dissolved in DMF (50 mL) under N2 and cooled to 0° C. DIEA (1.68 g, 13 mmol) was added, followed by the addition of 6-methyl-1,2,3,4-tetrahydroquinoline (1.91 g, 13 mmol). The reaction was stirred with gradual warming to RT. The reaction was quenched after 3 h with water, which causes a sticky precipitate to form. The mixture was extracted 3× with EtOAc. The EtOAc extracts were washed brine, combined, dried over Na2SO4, filtered, and concentrated, then dried under high vacuum to remove residual traces of DMF. The recovered material was purified by elution through a 17×2.5 cm column of silica gel (5%, 10%, 20% and 40% EtOAc/Hexane step gradient) giving 1-(4-chloro-[1,3,5]triazin-2-yl)-6-methyl-1,2,3,4-tetrahydro-quinoline as a white solid.

Provenance & Evidence