Water → HCID 136174530, compound

Participants

Reaction Steps

Potassium tert-butoxide (86 mg) was added to a solution of benzyl (3R)-3-[2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl]butylcarbamate (380 mg, 0.84 mmol) in 10 mL of THF. The reaction was stirred for about two hours at room temperature, and an analysis by thin layer chromatography (TLC) indicated the presence of starting material. Additional potassium tert-butoxide (120 mg) was added, and the reaction was stirred over three days at room temperature. CH2Cl2 (20 mL) and H2O (20 mL) were added. The layers were separated, and the organic fraction was washed sequentially with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 10-30% CMA/CHCl3) afforded (11S)-11-methyl-8,9,10,11-tetrahydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline (170 mg) as an off white solid.

Provenance & Evidence