Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1614958Generated: November 3, 2026

Water → 3-{(1S)-1-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenol

https://huagongshe.com/reaction/1614958

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantEthyl AcetateHCID 8857—
ReactantBoron tribromideHCID 25134—
Reactant{3-[(5-Chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanolHCID 58467829—
SolventDichloromethaneHCID 6344—
Product3-{(1S)-1-[(2-{[3-(Bromomethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]ethyl}phenolHCID 5846791975%

Reaction Steps

To a solution of {3-[(5-chloro-4-{[(1S)-1-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}methanol (0.30 g, 0.78 mmol) in methylene chloride (5.0 mL) was added slowly a solution of boron tribromide in methylene chloride (3.9 mL, 3.9 mmol, 1.0 M) at 0° C. The mixture was allowed to warm up to rt and stirred overnight. The resultant mixture was cooled in a dry ice bath when water was added. The mixture was allowed to warm up to rt. Water and EtOAc were added. The aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated (then triturated with cold EtOAc) to give the desired product as a white powder (0.255 g, 75%). LCMS for C19H19BrClN4O (M+H)+: m/z=433.0, 435.0.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08765727B2
Source datasetuspto-grants-2014_07
ORD IDord-2a377260dc37468c9bc60caf6a4b81c1
Source noteuspto-grants-2014_07