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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1924287Generated: November 2, 2026

Dimethylformamide → 4-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-one

https://huagongshe.com/reaction/1924287

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium hydrideHCID 24758—
ReactantHCID 17948959HCID 17948959—
Reactant3-(Chloromethyl)-6-methyl-2-phenylpyrazolo[1,5-a]pyrimidineHCID 57743008—
SolventWaterHCID 962—
Product4-(2,2-Difluorovinyl)-1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]pyrrolidin-2-oneHCID 5362913250%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08178533B2
Source datasetuspto-grants-2012_05
ORD IDord-3167f7fa5ecc4f08bfd75f06c088e018
Source noteuspto-grants-2012_05