Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 558546 | HCID 558546 | — |
| Reactant | 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile | HCID 13114183 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 70981147 | HCID 70981147 | 67% |
Reaction Steps
To a solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (750 mg, 4.0 mmol) in DMF (8 mL) was added 2-cyclopropylpropan-2-amine (400 mg, 4.0 mmol) and DIEA (1560 mg, 12.0 mmol). The resulting mixture was stirred at 60° C. for 2 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the crude product, which was purified by silica gel column chromatography (0-30% ethyl acetate in petroleum ether) to afford the title compound (665 mg, 2.68 mmol, 66% yield) as a white solid. MS (ESI) m/z=249.2 [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-3dddbee9700d45048b64aa5f2251847e |
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| Source note | uspto-grants-2015_09 |
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