HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 17948959 | HCID 17948959 | — |
| Reactant | 3-(Chloromethyl)-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine | HCID 57743008 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one | HCID 53629132 | 50% |
Reaction Steps
The above mentioned solution of intermediate x146 is added to a solution containing 4-(2,2-difluorovinyl)pyrrolidin-2-one x98 (2.64 mmol, 1.1 eq, 0.356 g), 6 ml of dry DMF and sodium hydride (60% dispersion in oil, 2.64 mmol, 1.1 eq, 0.1 g) that have been stirred at room temperature for 0.5 hour. The resulting mixture is heated up at 80° C. for 1 hour. The mixture is poured in water and extracted with AcOEt. The cumulated organic layers are washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue is crystallized in AcOEt to afford 0.443 g of 4-(2,2-difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one 211.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183241B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-112fb951bc23469dbc26fb1f3c5ef0b1 |
| Source note | uspto-grants-2012_05 |