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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1187681Generated: October 25, 2026

Toluene → (S)-4-Chloro-N-[1-(4-fluorophenyl)ethyl]-6-(pyridin-3-yl)pyrimidine-2-amine

https://huagongshe.com/reaction/1187681

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant3-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 4198005—
Reactant(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amineHCID 86659372—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product(S)-4-Chloro-N-[1-(4-fluorophenyl)ethyl]-6-(pyridin-3-yl)pyrimidine-2-amineHCID 8665938137.9%

Reaction Conditions

Temperature110 °C

Reaction Steps

500 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine (Reference Example 1), 314 mg of 3-(1,3,2-dioxaborinan-2-yl)pyridine, 927 mg of sodium carbonate and 202 mg of tetrakis(triphenylphosphine)palladium were added in turn to a degassed mixed solvent of 15 ml of toluene, 7 ml of ethanol and 10 ml of water, and the mixture was stirred at 110° C. for 3 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 218 mg of the objective compound as white powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08673891B2
Source datasetuspto-grants-2014_03
ORD IDord-9fd5aca10b844786bbdb5dd3a0ab5253
Source noteuspto-grants-2014_03