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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 709738Generated: October 25, 2026

Hydrochloric Acid → 4-Chloro-6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidine

https://huagongshe.com/reaction/709738

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium hydrideHCID 24758—
Reactant4,6-Dichloro-5-methoxypyrimidineHCID 78720—
Reactant(5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanolHCID 117759814—
SolventTetrahydrofuranHCID 8028—
Product4-Chloro-6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidineHCID 11776026394%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 4,6-dichloro-5-methoxypyrimidine (450 mg) and (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (760 mg) in THF (8.0 mL) was added 60% sodium hydride (200 mg) at 0° C., and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.05 g) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181186B2
Source datasetuspto-grants-2015_11
ORD IDord-509e63ab996b4640a72d67164b916ff6
Source noteuspto-grants-2015_11