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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1619440Generated: October 27, 2026

4,6-Dichloro-5-methylpyrimidine → 5-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

https://huagongshe.com/reaction/1619440

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4,6-Dichloro-5-methylpyrimidineHCID 818860—
Reactant1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OLHCID 21897744—
ReactantPotassium tert-butoxideHCID 23665647—
SolventTetrahydrofuranHCID 8028—
Product5-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazoleHCID 8659736662.5%

Reaction Conditions

Temperature30 °C

Reaction Steps

Potassium tert-butoxide (478 mg, 0.00426 moles) was added to a solution of 1-(3-iso-propyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol (0.9 gm, 0.00426 moles) and 4,6-dichloro-5-methylpyrimidine (690 mg, 0.00426 moles) in dry THF (30 ml) at 0° C. and the reaction mixture was stirred for 20 hours at 30° C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 900 mg product as off white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08772302B2
Source datasetuspto-grants-2014_07
ORD IDord-2596b292049147a481c0de98949b0136
Source noteuspto-grants-2014_07