HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | (S)-4-ethyloxazolidin-2-one | HCID 7832546 | — |
| Reactant | 3-Bromo-5-chloropyrazolo(1,5-a)pyrimidine | HCID 45480507 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one | HCID 67033956 | 56.3% |
Reaction Steps
To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (0.375 g, 1.61 mmol) and (S)-4-ethyloxazolidin-2-one (0.279 g, 2.42 mmol) in DMF (10 mL) was added sodium hydride (0.0968 g, 2.42 mmol) at ambient temperature. The mixture was stirred for 18 hours. Saturated aqueous NH4Cl was added and the solids were collected by filtration. Purification of the crude material by column chromatography (1-10% EtOAc in DCM) provided (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one (0.282 g, 56% yield) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08865726B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-efb800951b63423b9528848313f9d9e4 |
| Source note | uspto-grants-2014_10 |