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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 59158Generated: October 29, 2026

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

https://huagongshe.com/reaction/59158

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2-(Dicyclohexylphosphino)biphenylHCID 2734216—
Reactant3-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 45480181—
ReactantHCID 117821166HCID 117821166—
Catalystpalladium(II) acetateHCID 167845—
Product6-((Cyclopropylmethoxy)methyl)-N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-N4-methylpyrimidine-2,4-diamineHCID 86344615—

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of 2-chloro-6-((cyclopropylmethoxy)methyl)-N-methylpyrimidin-4-amine (41 mg, 0.18 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (73 mg, 0.36 mmol), cesium carbonate (117 mg, 0.36 mmol), palladium acetate (6 mg, 0.03 mmol) and 2-(dicyclohexyl-phosphino)biphenyl (9 mg, 0.03 mmol) was stirred under argon at 120° C. for 90 minutes in microwave oven. The mixture was filtered through a short silica gel plug which was washed with 10% solution of methanol in ethyl acetate (75 mL). The eluate was concentrated and the residue was purified by preparative HPLC to give the title compound as a dry film (30 mg, 42%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09439904B2
Source datasetuspto-grants-2016_09
ORD IDord-02c8479d3b5542c9a7d3b0fe598a1b0a
Source noteuspto-grants-2016_09