Methanol → 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

Participants

Reaction Steps

Iodotrimethylsilane (5.61 mL, 39.39 mmol) was added to 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (2.5 g, 7.88 mmol) in acetonitrile (25 mL) and the reaction stirred at RT for 20 hours. Methanol (15 mL) was added and stirred for 1 hour then a saturated solution of sodium thiosulphate (10 mL) was added and stirred for a further 20 mins. The volatiles were removed in vacuo and the aqueous residue extracted into ethyl acetate (2×150 mL). The organics were washed with water (100 mL), brine (100 mL), dried (MgSO4), and reduced in vacuo to give the desired compound as a white solid (2.03 g). 1H NMR δ (d6-DMSO): 1.22 (d, 3H), 2.48 (s, 3H), 3.44-3.59 (m, 2H), 4.50 (sextet, 1H), 4.87 (t, 1H), 6.53 (t, 1H), 6.98 (s, 1H), 7.11 (s, 1H), 8.36 (s, 1H), 9.25 (s, 1H), 9.75 (s, 1H), 10.89 (s, 1H); m/z 304 (M+H)+

Provenance & Evidence