Methyl iodide → HCID 58739060, compound

Participants

Reaction Steps

A solution of 5-methoxy-2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.442 g, 1.81 mmol) in dry N,N-dimethylformamide (5 ml) was treated at 10° C. with sodium hydride (0.080 g of a 60% dispersion in mineral oil, 2.0 mmol) and the resulting mixture was stirred for 10 min. Then iodomethane (0.123 ml, 2.0 mmol) was added and the mixture was stirred for another 1 h. The solvent was then evaporated in vacuo and the residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 9:1) gave 0.419 g (89% yield) of the title ester as white needles; mp 74.5–76° C. (ether-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.41 (3H, t, J=7.1 Hz, CH3), 2.62 (3H, s, SCH3), 3.55 (3H, s, NCH3), 3.95 (3H, s, OCH3), 4.43 (2H, q, J=7.1 Hz, CH2). Anal. Calcd for C10H14N2O4S: C 46.50, H 5.46; N, 10.85. Found: C 46.73; H, 5.21; N, 10.93.

Provenance & Evidence