m-Chloroperbenzoic acid → N-[[(1-Methylethyl)amino]carbonyl]-4-(methylsulfinyl)-2-amino-5-pyrimidinesulfonamide

Participants

Reaction Steps

2-Amino-N-[[(1-methylethyl)amino]carbonyl]-4-(methylthio)-5-pyrimidinesulfonamide (3.0 g, 9.84 mmol) was dissolved in dry (freshly distilled from sodium/benzophenone) THF (60 mL) and m-chloroperbenzoic acid (MCPBA) (2.55 g, 11.81 mmol, 80% 1.2 eq) was added as a solid. The reaction turned yellow and a white solid precipitated out of solution. After 90 minutes the reaction was diluted with ethyl ether (60 mL) and the white solid was filtered, washed with THF, then with ether three times and air dried for 2 hours, to yield 2.64 g (8.22 mmol, 84%) of product, m.p. 140° C. (dec.). The product was unstable to heat but could be stored under nitrogen in the freezer for weeks.

Provenance & Evidence