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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 59161Generated: October 29, 2026

Cesium carbonate → N4-(Cyclopropylmethyl)-N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-2,4-diamine

https://huagongshe.com/reaction/59161

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2-(Dicyclohexylphosphino)biphenylHCID 2734216—
Reactant3-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 45480181—
ReactantHCID 117821080HCID 117821080—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
ProductN4-(Cyclopropylmethyl)-N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-2,4-diamineHCID 86345163—

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (99 mg, 0.49 mmol), 2-chloro-N-(cyclopropylmethyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (72 mg, 0.24 mmol), cesium carbonate (159 mg, 0.49 mmol), palladium(II) acetate (8.20 mg, 0.04 mmol) and 2-(dicyclohexylphosphino)biphenyl (12.80 mg, 0.04 mmol) in dioxane (1.5 mL) was heated at 120° C. by microwave irradiation under nitrogen atmosphere for 90 minutes. The mixture was filtered through diatomeous earth, the pad was eluted with methanol. The eluate was concentrated and the residue was purified by preparative chromatography to give the title compound as a dry film, 65 mg (58%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09439904B2
Source datasetuspto-grants-2016_09
ORD IDord-b2fc31521de7494ea7f4779117991f01
Source noteuspto-grants-2016_09