Triphenylphosphine → HCID 57545330, compound

Participants

Reaction Conditions

Reaction Steps

5-(Ethoxymethyl)-6-(2-methylpropyl)-8-(pyridin-3-ylmethoxy)-6H-imidazo[4,5-c]tetraazolo[1,5-α]quinoline (300 mg, 0.69 mmol) and triphenylphosphine (1 g, 4.17 mmol) were combined in a sealed vial and heated at 150° C. with stirring for 4 hours. The reaction was cooled to ambient temperature; diluted with chloroform; and purified by flash column chromatography on silica eluting with 5-10% gradient of methanol in chloroform. The clean fractions were concentrated under vacuum to provide a brown solid. This solid was refluxed for 1 hour in 4 mL of 3M aqueous HCl. The pH was adjusted to 14 by adding solid potassium hydroxide, and the resulting precipitate was filtered. The solid was dried under reduced pressure to provide 2-ethoxymethyl-1-(2-methylpropyl)-8-(pyridin-3-ylmethoxy)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 204.0-206.0° C.

Provenance & Evidence