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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2103975Generated: October 25, 2026

Benzyl Bromide → 4-Methyl-6-phenethylpyrimidine

https://huagongshe.com/reaction/2103975

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzyl BromideHCID 7498—
Reactant4,6-DimethylpyrimidineHCID 15257—
ReactantAmmonium ChlorideHCID 25517—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product4-Methyl-6-phenethylpyrimidineHCID 1783065585.7%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of 4,6-dimethylpyrimidine (1.08 g, 10 mmol) in THF (40 ml) was added dropwise at −78° C. a solution of n-butyllithium. To the solution was added benzylbromide (1.71 g, 10 mmol). The mixture was warmed up to 0° C. and stirred for 30 minutes. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate). The obtained fraction was concentrated to give 4-methyl-6-phenethylpyrimidine (1.7 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07576198B1
Source datasetuspto-grants-2009_08
ORD IDord-3c1a31d358414febb65bf4ca424f7e35
Source noteuspto-grants-2009_08