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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 74936Generated: October 26, 2026

Ethyl Acetate → 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S)-3-methoxycyclohexyl)pyrimidin-4-amine

https://huagongshe.com/reaction/74936

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-N-(3-methoxycyclohexyl)pyrimidin-4-amineHCID 67285658—
Reactant2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S)-3-methoxycyclohexyl)pyrimidin-4-amineHCID 68007568—
CatalystSodium MethoxideHCID 10942334—
SolventTetrahydrofuranHCID 8028—
SolventSodium chloride; waterHCID 57417360—
Product2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-((1S)-3-methoxycyclohexyl)pyrimidin-4-amineHCID 68007359—

Reaction Steps

To a solution of 2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-N-(3-methoxycyclohexyl)pyrimidin-4-amine, 27b, (0.08 g, 0.15 mmol) in THF were added a few drops of NaOMe. The reaction mixture was stirred at room temperature for 20 min. To the reaction mixture was added ethyl acetate and brine. The organic phase was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in CH3CN/H2O and the mixture was purified by preparatory HPLC to afford 23 mg of the desired product, 552.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829007B2
Source datasetuspto-grants-2014_09
ORD IDord-44b3b40720c746c4939eee667b727cfb
Source noteuspto-grants-2014_09