HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 714815Generated: October 30, 2026
Cesium carbonate → 1-(2-Chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile
https://huagongshe.com/reaction/714815
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | 3-Cyclopropyl-2-oxopyrrolidine-3-carbonitrile | HCID 91618631 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(2-Chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile | HCID 117839802 | 76.7% |
Reaction Steps
To a mixture of 3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile (18 g) obtained in Step C of Example 103, 2,4-dichloropyrimidine (17 g), cesium carbonate (76 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (4.1 g) in tetrahydrofuran (300 mL) was added tris(dibenzylideneacetone)dipalladium(0) (2.1 g), and the mixture was stirred overnight at 85° C. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (23 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187453B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-0407b204fb6046408ac3be18a6c0494b |
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| Source note | uspto-grants-2015_11 |
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