Sodium Methoxide → HCID 67173009, compound

Participants

Reaction Steps

2-(1-((5-Bromopyridin-2-yl)methyl)ureido)acetate (9J2) (35.0 mmol, 11.08 g) was dissolved in dry methanol (150 ml), and sodium methoxide (70.1 mmol, 3.79 g) added and the solution stirred at room temperature for 3 hours. The reaction was quenched with water and acidified with saturated ammonium chloride solution to ˜pH 7. The mixture was extracted with DCM (3×) and the combined organics washed with brine and dried over sodium sulphate, filtered and concentrated to afford a crude product which was purified on silica eluting with Heptane/EtOAc/EtOH 5/4/1 to give 1-((5-bromopyridin-2-yl)methyl)imidazolidine-2,4-dione. (9J3) 6.12 g (64%); 1H NMR (400 MHz, CDCl3) 8.68 (bs, 1H) 8.63 (d, 1H) 7.86 (dd, 1H) 7.22 (d, 1H) 4.61 (s, 2H) 4.04 (s, 2H).

Provenance & Evidence