Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 59138Generated: October 27, 2026

Nitrogen → N4-Isopropyl-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/59138

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantCesium carbonateHCID 10796—
Reactant2-(Dicyclohexylphosphino)biphenylHCID 2734216—
Reactant3-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 45480181—
Reactant2-Chloro-N-isopropyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amineHCID 117821089—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
ProductN4-Isopropyl-N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-2,4-diamineHCID 8634424760.5%

Reaction Conditions

Temperature120 °C

Reaction Steps

3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (90 mg, 0.44 mmol), 2-chloro-N-isopropyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (63 mg, 0.22 mmol), cesium carbonate (145 mg, 0.44 mmol), palladium acetate (7.48 mg, 0.03 mmol) and 2-(dicyclohexylphosphino)-biphenyl (11.68 mg, 0.03 mmol) in dioxane (1.5 mL) were mixed in a vial under N2 atmosphere. The mixture was heated at 120° C. in a microwave reactor for 90 minutes. The mixture was filtered through diatomeous earth and the filter plug was washed with methanol. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound as a solid 60 mg (60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09439904B2
Source datasetuspto-grants-2016_09
ORD IDord-a1622811e49b4642bf9da8d75fff171f
Source noteuspto-grants-2016_09