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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 469298Generated: October 25, 2026

Sodium hydride → (4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

https://huagongshe.com/reaction/469298

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant4,6-DichloropyrimidineHCID 70943—
Reactant4-(Benzyloxy)-3,5-dimethylbenzaldehydeHCID 563557—
Reactant1,3-Dimethyl-1H-benzimidazol-3-ium iodideHCID 11821793—
SolventTetrahydrofuranHCID 8028—
Product(4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanoneHCID 58181140—

Reaction Steps

150 mg (1.00 mmol) 4,6-dichloropyrimidine, 367 mg (1.50 mmol) 4-benzyloxy-3,5-dimethylbenzaldehyde and 166 mg (0.600 mmol) 1,3-dimethyl-3H-benzimidazol-1-ium-iodide (Chem. Pharm. Bull. 1990, 1147-52) in 10.0 mL THF were stirred at RT. Then 73.0 mg (1.51 mmol) sodium hydride (50% in mineral oil) were added and the reaction mixture was refluxed for 2.5 h. The reaction mixture was added to ice water and extracted with DCM. The organic phase was dried and evaporated down.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08629137B2
Source datasetuspto-grants-2014_01
ORD IDord-2b99befe98664d19803e34af9b5504b7
Source noteuspto-grants-2014_01