Sodium Hydroxide → 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyl-5-bromo-1H-pyrimidine-2,4-dione (1.0 g, 3.6 mmol) in N,N-dimethylformamide (15 mL) was added tetrabutylammonium bromide (46 mg, 0.14 mmol) and sodium hydroxide (160 mg, 3.9 mmol). The suspension was stirred vigorously, heated to 60° C. for 1.5 h and then cooled to ambient temperature. N-tert-butoxycarbonyl-3-bromopropylamine (0.93 g, 3.9 mmol) was added, the reaction was heated to 50° C. for 20 h and then concentrated in vacuo. The residue was taken up in ethyl acetate:water (1:1 100 mL), the layers separated and the aqueous layer extracted with ethyl acetate (3×50 mL). The organic layers were combined and washed with 0.5 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 (40% ethyl acetate in hexane) to provide 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dione.

Provenance & Evidence