Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile | HCID 13114183 | — |
| Reactant | 1-ethylcyclopentanamine hydrochloride | HCID 75530782 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 71237256 | HCID 71237256 | 60.4% |
Reaction Steps
To a stirring solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (984 mg, 5.3 mmol) in DMSO (10 mL) was added DIEA (2.1 g, 15.9 mmol) and 1-ethylcyclopentanamine hydrochloride (900 mg crude). The resulting mixture was stirred at 60° C. for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. The crude product was purified by silica gel column chromatography (5% ethyl acetate in petroleum ether) to get the desired product as a yellow oil (830 mg, 3.2 mmol, 53.5% yield). MS (ESI) m/z=263.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09139534B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-d62c4f3c37324659966aa59ceb24fe94 |
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| Source note | uspto-grants-2015_09 |
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