Hydrochloric Acid → HCID 54353644, compound

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.

1. additionwere added
2. temperaturecooling
3. stirringwith stirring
4. stirringthe resulting mixture was stirred at room temperature for 1 hour
5. extractionextracted three times with chloroform
6. washThe combined organic layer was washed with a saturated aqueous sodium chloride twice
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was evaporated under reduced pressure
9. temperaturewas heated
10. temperatureunder reflux for 3 hours
11. temperatureThe mixture was then cooled
12. extractionextracted three times with chloroform
13. washThe extracts were washed with a saturated aqueous sodium chloride
14. dry with materialdried over anhydrous magnesium sulfate
15. customthe solvent was evaporated under reduced pressure
16. customThe residue was purified by silica gel column chromatography (eluent: 4% methanol/chloroform)
17. customrecrystallized from hexane/toluene

ORD record

ord-2136e78e6c1943c0b2832272729f42fe

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05395836