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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 242274Generated: October 27, 2026

Trifluoroacetic acid → 2-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

https://huagongshe.com/reaction/242274

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant4-Chloro-6-hydrazinylpyrimidineHCID 247222—
ReactantEthyl 3-(dimethylamino)-2-(1H-1,2,3-triazol-1-yl)acrylateHCID 66726233—
SolventEthanolHCID 702—
Product2-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochlorideHCID 86635254—

Reaction Conditions

Temperature100 °C

Reaction Steps

1.1 ml (1.6 g, 13.8 mmol) TFA are added to a mixture of 7.3 g (34.6 mmol) of the compound from Example 3A and 6.0 g (41.5 mmol) of the compound from Example 7A in 70 ml ethanol and the mixture is stirred at 100° C. for 20 h. The solid which has precipitated out is filtered off and the filtrate is concentrated in vacuo. The residue is suspended in 100 ml ethanol, 30 ml of a 30% strength sodium methanolate solution in methanol are added and the mixture is stirred at RT for 1.5 h. After addition of 42 ml of a 4 N solution of hydrogen chloride in dioxane (pH=5-6) and after stirring for 30 min, the solid is filtered off, washed first with ethanol and then with diethyl ether and dried in vacuo. Further purification is carried out by stirring in ethanol and acetonitrile several times. 10 ml of a 4 N solution of hydrogen chloride in dioxane are then added and the mixture is stirred at RT for 16 h. The product is filtered off, washed first with acetonitrile and then with diethyl ether and dried in vacuo.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08653111B2
Source datasetuspto-grants-2014_02
ORD IDord-eb995479adbb4eefa154e060b3b6dd8b
Source noteuspto-grants-2014_02