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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1021709Generated: October 30, 2026

Cesium carbonate → 6-Chloro-4-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-2-methylpyridazin-3(2H)-one

https://huagongshe.com/reaction/1021709

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant6,7-dihydro-4H-pyrazolo(5,1-c)(1,4)oxazin-2-amineHCID 58043799—
Reactant4-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-oneHCID 59216474—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Product6-Chloro-4-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-2-methylpyridazin-3(2H)-oneHCID 5804378881%

Reaction Steps

A mixture of 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amine 129b (0.8 g, 5.76 mmol), xantophos (360 mg, 0.623 mmol), Pd2dba3 (384 mg, 0.42 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (1.28 g, 5.76 mmol) and Cs2CO3 (5.05 g. 17.3 mmol) in 1,4-dioxane (40 mL) was heated at reflux for 2 h. After the completion of the reaction, the mixture was filtered off, and washed with MeOH (60 mL). The filtrate was evaporated in vacuo. The residue was purified on reverse phase Combi-flash to give 132a (1.3 g, 81%). MS: [M+H]+ 282.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08716274B2
Source datasetuspto-grants-2014_05
ORD IDord-74f1becbe11744a0ae47d64bde09431c
Source noteuspto-grants-2014_05