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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 403469Generated: October 25, 2026

Sodium hydride → tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate

https://huagongshe.com/reaction/403469

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant(1R,2R)-2-fluorocyclohexan-1-olHCID 12700773—
ReactantTert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetateHCID 86679896—
SolventDimethylformamideHCID 6228—
Producttert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetateHCID 8667989993.7%

Reaction Steps

26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08748436B2
Source datasetuspto-grants-2014_06
ORD IDord-24f43d1ec1624cc4a7a461ab0bc7b292
Source noteuspto-grants-2014_06