Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Exo-2-bornanamine | HCID 98480 | — |
| Reactant | 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile | HCID 13114183 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53735900 | HCID 53735900 | 64% |
Reaction Steps
To a 0° C. solution of 10.0 g (53.9 mmol) of 4-chloro-2-(methylthio)-5-pyrimidinecarbonitrile in 100 mL of dichloromethane is added 9.0 mL (64.6 mmol) of triethylamine followed by dropwise addition of 7.0 mL (59.3 mmol) of exo-2-aminonorbornane. The reaction mixture is stirred at 0° C. for 2 hours. The resulting precipitate of triethylamine hydrochloride is filtered. The filtrate is washed three times with saturated aqueous solution of sodium bicarbonate. The aqueous phase is back extracted twice with dichloromethane. The combined organic phase is concentrated, and the residue is purified by filtering through a short column of silica gel eluted with dichloromethane to give 8.9 g (64%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07501425B1 |
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| Source dataset | uspto-grants-2009_03 |
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| ORD ID | ord-dea467a11b1a407496123b0c2715f76e |
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| Source note | uspto-grants-2009_03 |
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