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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2240263Generated: October 29, 2026

Dimethylformamide → 6-Chloro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine

https://huagongshe.com/reaction/2240263

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium HydroxideHCID 14798—
Reactant2-Amino-4,6-dichloropyrimidineHCID 65522—
Reactant3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)anilineHCID 59305033—
SolventHydrochloric AcidHCID 313—
SolventWaterHCID 962—
Product6-Chloro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]pyrimidine-2,4-diamineHCID 86624341—

Reaction Steps

40 mg (0.15 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline and 29 mg (0.18 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 2 ml of water and 0.11 ml of 2N hydrochloric acid. The reaction mixture is heated at reflux for 15 hours. After cooling, the mixture is made alkaline using dilute aqueous sodium hydroxide solution, a little DMF is added and the mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07723347B2
Source datasetuspto-grants-2010_05
ORD IDord-5ede3aec739b472c823b971a2d21b95e
Source noteuspto-grants-2010_05