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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75417Generated: October 26, 2026

Sodium hydride → 4-[4-Isopropoxy-6-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-pyrimidin-2-yl]-phenylamine

https://huagongshe.com/reaction/75417

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant3-[6-Chloro-2-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octaneHCID 86665884—
ReactantHCID 178418361HCID 178418361—
SolventIsopropanolHCID 3776—
Product4-[4-Isopropoxy-6-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-pyrimidin-2-yl]-phenylamineHCID 66750665—

Reaction Conditions

Temperature140 °C

Reaction Steps

In a 2-5 mL microwave vial was placed 3-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (13, 70 mg, 0.202 mmol) in 2-propanol (4 mL) to give a yellow suspension. Sodium hydride (60% in oil, 32.3 mg, 0.807 mmol) was added and the mixture was stirred until no further formation of hydrogen gas was observed. The reaction was heated under microwave irradiation at 140° C. for 30 min to give a bright orange suspension. Work-up: the solvents were evaporated. The residue was dissolved in dichloromethane and washed with sat NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound in a quantitative yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835429B2
Source datasetuspto-grants-2014_09
ORD IDord-b13fb660e2a540fdbacf5424beaf4f4a
Source noteuspto-grants-2014_09