HCID 57550527, compound → HCID 57550541, compound

Participants

Reaction Steps

1-(2,4-Diamino-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (0.50 g, 1.8 mmol), trifluoroacetic acid (200 mL), and platinum (IV) oxide (300 mg) were added to a Parr vessel and shaken under hydrogen pressure (45 psi, 3.1×105 Pa) for eight days. The volatiles were removed under reduced pressure, and the residue was dissolved in methanol and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure, and the resulting solid was dissolved in methanol. Hydrogen chloride (30 mL of a 4 M solution in dioxane) was added, and the resulting solution was stirred for two hours. Ammonia (7 M in methanol) was added, and the volatiles were then removed under reduced pressure. Ammonia (7 M in methanol was added a second time, and the resulting mixture was concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica cartridge, eluting with 0-8% methanol in dichloromethane with aqueous ammonium hydroxide added). The resulting white solid was washed with hot acetonitrile and dried in a vacuum oven to provide 280 mg of 1-(2,4-diamino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white solid, mp >270° C.

Provenance & Evidence