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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2214456Generated: November 1, 2026

Cesium carbonate → 2-Bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

https://huagongshe.com/reaction/2214456

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2-(Chloromethyl)-4-methylquinazolineHCID 241518—
Reactant2-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-oneHCID 21947658—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product2-Bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-oneHCID 16037778—

Reaction Conditions

Temperature80 °C

Reaction Steps

489 mg (1.5 mmol) of caesium carbonate were added to a solution of 300 mg (1.12 mmol) of 2-bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and 260.1 mg (1.35 mmol) of 2-chloromethyl-4-methyl-quinazoline in 4.0 ml of dimethylformamide and this mixture was stirred for 2 hours under an argon atmosphere at 80° C. Then it was diluted with 10 ml of water and stirred for 30 minutes at ambient temperature. The crude product precipitated was suction filtered and purified by column chromatography (silica gel; eluant:petroleum ether with 20–50% ethyl acetate).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07109192B2
Source datasetuspto-grants-2006_09
ORD IDord-0076b42d6ff141e5a639ced9c6c6aaab
Source noteuspto-grants-2006_09