Hydrochloric Acid → HCID 54353644, compound

Participants

Reaction Steps

To a solution of 1.10 g (5.61 mmol) of 3-hydroxy-1-adamantane carboxylic acid (3-hydroxy-1-tricyclo [3.3.1.13,7 ]decane carboxylic acid) [Syn. Commun. 18, 1967 (1988)] in a mixture of 10 ml-methylene chloride and 25 ml-dimethyl formamide, 1.03 g (6.73 mmol) of 1-hydroxy benzotriazole and 1.61 g (8.42 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide were added and stirred at room temperature for 30 minutes. To the reaction mixture was added dropwise 15 ml of a solution of 5,6-diamino-1,3-dipropyluracil in methylene chloride under ice-cooling and with stirring, and the resulting mixture was stirred at room temperature for 1 hour. 50 ml of a saturated aqueous sodium bicarbonate was added to the resulting mixture and extracted three times with chloroform. The combined organic layer was washed with a saturated aqueous sodium chloride twice and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. A suspension of the obtained residue and calcium hydroxide (2.77 g, 37 mmol) in 35 ml of water was heated under reflux for 3 hours. The mixture was then cooled, adjusted to pH 2 with concentrated hydrochloric acid, and extracted three times with chloroform. The extracts were washed with a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 4% methanol/chloroform), and recrystallized from hexane/toluene to give 680 mg (yield 33%) of Compound 8 as a white plate crystal.

Provenance & Evidence