1,3-Dibromopropane → 1-benzyl-3-(3-bromopropyl)-5-methyl-1H-pyrimidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyl-5-methyl-1H-pyrimidine-2,4-dione (1.0 g, 4.6 mmol) in N,N-dimethylformamide (15 mL) was added tetrabutylammonium bromide (60 mg, 0.2 mmol) and sodium hydroxide (200 mg, 5.1 mmol). The suspension was stirred vigorously, heated to 60° C. for 1.5 h and then cooled to ambient temperature. 1,3-Dibromopropane (0.5 mL, 5.1 mmol) was added, the reaction was heated to 50° C. for 16 h and then concentrated in vacuo. The residue was taken up in ethyl acetate:water (1:1 200 mL), the layers separated and the aqueous layer extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with 1 M sodium hydroxide (1×50 mL), water (1×50 mL), brine (1×100 mL), dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified by pressurized silica gel chromatography (25-30% ethyl acetate in hexane) to provide 1-benzyl-3-(3-bromopropyl)-5-methyl-1H-pyrimidine-2,4-dione.

Provenance & Evidence