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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 709734Generated: October 30, 2026

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

https://huagongshe.com/reaction/709734

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium hydrideHCID 24758—
Reactant4,6-Dichloro-5-methylpyrimidineHCID 818860—
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-methylpyrimidineHCID 11776011780.6%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 4,6-dichloro-5-methylpyrimidine (160 mg) and (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (300 mg) in THF (8.0 mL) was added 60% sodium hydride (60 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 (340 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181186B2
Source datasetuspto-grants-2015_11
ORD IDord-d68757376dbb416fbcd8bfd7b2b4f4f4
Source noteuspto-grants-2015_11