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 | 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid | HCID 11042062 | — |
| Reactant | HCID 11994282 | HCID 11994282 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22219469 | HCID 22219469 | 80.1% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07022686B2 |
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| Source dataset | uspto-grants-2006_04 |
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| ORD ID | ord-17d62afcf8664f4abb1525f50ee56276 |
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| Source note | uspto-grants-2006_04 |
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