Hydrochloric Acid → HCID 11994283, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Water	HCID 962	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 11994282	HCID 11994282	—
Reactant	4-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid	HCID 12560136	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 11994283	HCID 11994283	38.7%

Reaction Steps

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (3.4 g) was dissolved in 80 mL of DMF along with 4-hydroxy-bicyclo[2.2.2]octane-1-carboxylic acid (2.5 g, 15 mmol). HATU (5.9 g, 1.05 eq) was added, followed by Et3N (8.30 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The teaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 60 mL of H2O containing 10 eq of NaOH (5.9 g). The reaction mixture was stirred under reflux for 1 h, cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 1.85 g of the xanthine derivative.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06605601B2
Source dataset	uspto-grants-2003_08
ORD ID	ord-bb460ba758474a3b8999f66300133291
Source note	uspto-grants-2003_08