Hydrochloric Acid → Methyl 2-(6-(methylthio)pyrimidin-4-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(6-methylsulfanyl-pyrimidin-4-yl)-malonic acid dimethyl ester 3 (3.35 g, 13 mmol) and sodium methoxide (0.300 ml of 25% w/v solution, 1.30 mmol, 0.1 eq.) in MeOH (100 ml) is heated at 60° C. for 3 hours. The reaction mixture is cooled to room temperature, neutralized with 1N HCl solution (1.30 mL) and concentrated. The residue, is extracted with ethyl acetate. The organic layer is washed with brine and dried over Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 50% to afford (6-methylsulfanyl-pyrimidin-4-yl)-acetic acid methyl ester as a yellow oil. 1H NMR 400 MHz (CDCl3) δ 8.86 (s, 1H), 7.18 (s, 1H), 3.73 (s, 3H), 3.70 (s, 2H), 2.55 (s, 3H).

Provenance & Evidence