Sodium hydride → HCID 67205423, compound

Participants

Reaction Steps

Under a nitrogen atmosphere 2-mercaptopyridine (1.23 g, 11.1 mmol) was added to a suspension of sodium hydride (0.41 g of 60%, 10 mmol) in DMF (30 mL). After hydrogen evolution had ceased, 1-[2-(3-chloropropoxy)ethyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.20 g, 9.23 mmol) was added. After 2 hours analysis by HPLC indicated that starting material remained. 2-Mercaptopyridine (0.30 g) and sodium hydride (0.10 g) were added. After 3.5 hours the reaction mixture was poured into water with rapid stirring. The resulting brown solid was isolated by filtration and then triturated with diethyl ether to provide 3.71 g of 2-propyl-1-(2-{3-[(pyridin-2-yl)thio]propoxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid.

Provenance & Evidence