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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 56452Generated: October 25, 2026

Cesium carbonate → 2,8-Dichloro-6-(3,5-dimethoxyphenyl)quinazoline

https://huagongshe.com/reaction/56452

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant(3,5-Dimethoxyphenyl)boronic acidHCID 4374257—
Reactant6-Bromo-2,8-dichloroquinazolineHCID 59199294—
CatalystHCID 178418476HCID 178418476—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product2,8-Dichloro-6-(3,5-dimethoxyphenyl)quinazolineHCID 11803617441.2%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 6-bromo-2,8-dichloroquinazoline (4.0 g, 14.5 mmol), 3,5-dimethoxyphenylboronic acid (4.23 g, 16.0 mmol), cesium carbonate (9.42 g, 29.0 mmol) and Pd(PPh3)2Cl2 (220 mg, 0.70 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 5 hours. The reaction mixture was cooled to room temperature, directly concentrated and purified by silica gel chromatography (petroleum ether: dichloromethane=2:1˜1:1) to get the title compound as a yellow solid (2.0 g, 41%). MS (ES+) C16H12Cl2N2O2 requires: 334, 336, found: 335, 337 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434700B2
Source datasetuspto-grants-2016_09
ORD IDord-b6cf8aadc9494aa89770cc412d30f3d1
Source noteuspto-grants-2016_09