Potassium Carbonate → 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

The crude product from step 1 (3.0 g, 14.8 mmol) was dissolved in N,N-dimethylformamide (30 mL) and treated with potassium carbonate (4.08 g, 29.6 mmol) and 2-fluorobenzyl bromide (Aldrich) (1.8 ml, 14.8 mmol). The reaction was stirred at 23° C. for 2 hours and then at 48° C. for 3 hours. The reaction was mixed with diluted brine and extracted with ethyl acetate (3×). The combined ethyl acetate extracts were then washed with diluted aqueous sodium chloride solution and brine, dried (sodium sulfate) and concentrated to dryness to afford 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione as a yellow oil (4.07 g, 89%). 1H NMR (CDCl3, 200 MHz) δH 0.96 (t, 3H), 1.25–1.48 (m, 2H), 1.58–1.76 (m, 2H), 4.03 (t, 2H), 5.20 (s, 2H), 5.97 (s, 1H), 6.97–7.10 (m, 2H), 7.17–7.30 (m, 2H).

Provenance & Evidence