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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 279659Generated: October 30, 2026

Thionyl Chloride → 4-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochloride

https://huagongshe.com/reaction/279659

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-oneHCID 135671176—
SolventTolueneHCID 1140—
SolventDimethylformamideHCID 6228—
Product4-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochlorideHCID 2262490590%

Reaction Steps

A mixture of 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-one (250 mg, 0.73 mmol) in thionyl chloride (5 ml) and DMF (0.1 ml) was heated at reflux for 1 hour. The mixture was diluted with toluene and the volatiles were removed by evaporation. The residue was triturated with methylene chloride/ether, the solid was collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochloride (260 mg, 90%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06362336B1
Source datasetuspto-grants-2002_03
ORD IDord-16150b27b5a4447a9706f2a041ea241c
Source noteuspto-grants-2002_03