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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 562483Generated: October 30, 2026

Trifluoroacetic acid → 1-{2-[6-(1,2-Oxazinan-2-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-imidazole-4-carbonitrile

https://huagongshe.com/reaction/562483

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-Chloro-6-hydrazinylpyrimidineHCID 247222—
Reactant1,2-Oxazinane hydrochlorideHCID 13010712—
ReactantEthyl 3-(N,N-dimethylamino)-2-(4-cyano-1H-imidazol-1-yl)acrylateHCID 66726020—
SolventWaterHCID 962—
Product1-{2-[6-(1,2-Oxazinan-2-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-imidazole-4-carbonitrileHCID 44465131—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 205 mg (1.7 mmol) of 1,2-oxazinane hydrochloride [Bhat et al., J. Chem. Soc. Perkin Trans. 2 2000, 7, 1435-1446] and 289 μl (215 mg, 1.7 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 1.5 h. Following the addition of 59 μl (49 mg, 0.4 mmol) of trifluoroacetic acid and 324 mg (1.4 mmol) of the compound from Example 6A, the reaction mixture is stirred at 100° C. for 16 h. The precipitated solid is filtered off and washed first with water and then with diethyl ether. The product is dried under reduced pressure. Yield: 199 mg (39% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067407B2
Source datasetuspto-grants-2011_11
ORD IDord-8c45433329ec404484d6a3c65b869fd6
Source noteuspto-grants-2011_11