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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2195084Generated: November 1, 2026

Dimethylformamide → 6-{4-[6-(4-Fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-chloro-nicotinonitrile

https://huagongshe.com/reaction/2195084

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant4-[4-(5-Bromo-3-chloro-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidineHCID 59168342—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
Product6-{4-[6-(4-Fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-chloro-nicotinonitrileHCID 59168376—

Reaction Steps

To a mixture of 4-[4-(5-bromo-3-chloro-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(S)-methyl-pyrrolidin-1-yl)-pyrimidine (700 mg) and Zn(CN)2 (94 mg) in DMF, add Pd(PPh3)4 (77 mg, 0.067 mmol). Purge the reaction mixture for 10 min with dry N2. Heat the stirring reaction mixture overnight at 80° C., cool to room temperature and partition between water and EtOAc. Dry the solution (Na2SO4), concentrate under reduced pressure. Purify the residue by flash column eluting with EtOAc-Hexanes (1:1) to afford the title compound as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08334382B2
Source datasetuspto-grants-2012_12
ORD IDord-d0727776d03e412fb1f5d72e1ec6da3a
Source noteuspto-grants-2012_12