Hydrochloric Acid → HCID 22219469, compound

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (570 mg) was dissolved in 20 mL of DMF along with bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (520 mg, 2.45 mmol). HATU (980 mg, 1.05 eq) was added, followed by Et3N (1.40 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The following morning, the reaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 10 mL of H2O containing 10 eq of NaOH (980 mg). The reaction mixture was stirred under reflux for 2 h. It was then cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 680 mg of the acid derivative.

1. customThe resulting reaction mixture
2. filtrationThe following morning, the reaction mixture was filtered
3. customto remove some of the precipitate
4. concentrationThe filtrate was concentrated under reduced pressure
5. stirringThe reaction mixture was stirred
6. temperatureunder reflux for 2 h
7. temperatureIt was then cooled to rt
8. filtrationThe resulting precipitate was collected by filtration
9. customdried

ORD record

ord-17d62afcf8664f4abb1525f50ee56276

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022686B2