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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 339751Generated: October 28, 2026

Ethyl 5-(chloromethyl)-2-furancarboxylate → Ethyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylate

https://huagongshe.com/reaction/339751

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl 5-(chloromethyl)-2-furancarboxylateHCID 263166—
ReactantSodium BicarbonateHCID 516892—
Reactant4-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidineHCID 68002449—
SolventDimethylformamideHCID 6228—
ProductEthyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylateHCID 44815753—

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 4-amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine (2.8 g), ethyl 5-chloromethyl-2-furancarboxylate (1.8 g), sodium hydrogencarbonate (1 g) and N,N-dimethylformamide (120 ml) was heated while stirring at 80° C. for 12 hours. The mixture thus obtained was concentrated under reduced pressure. To the resultant residue, water was added. After extraction was performed with ethyl acetate, an organic phase was dried over anhydrous sodium sulfate and evaporated. The resultant residue was purified by column chromatography to obtain a target substance (0.8 g). The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08895565B2
Source datasetuspto-grants-2014_11
ORD IDord-2907cf1254374dbe92dbc86c26587b03
Source noteuspto-grants-2014_11