Tetrabutylammonium Fluoride → HCID 21186225, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (0.4 ml of a 1.0 M solution in THF) was added to a solution of 2-[4-(2-((tert-butyldimethylsiloxy)methyl)propyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (118 mg) in THF (5 ml) at ambient temperature. More tetrabutylammonium fluoride solution was added after 0.25 hour (0.4 ml), after 0.75 hour (1.0 ml) and finally after 1.5 hours (0.2 ml). The reaction mixture was stirred for a further 0.5 hour, diluted with water (10 ml) and the reaction mixture was extracted with dichloromethane (4×10 ml). The combined organic extracts were dried over MgSO4 and evaporated to give an amber oil. This was purified by gradient elution with 0-50% methanol/dichloromethane through a silica gel Mega Bond Elut column to give 2-[4-(3-hydroxy-2-methylpropyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (75 mg) as a white crystalline solid, m.p. 118-119° C.; 1H NMR (DMSO-d6): 0.95 (d, 3H), 1.35 (m, 1H), 2.0 (m, 1H), 2.3 (s, 3H), 2.5 (m, 1H), 2.9 (m, 1H), 3.5 (m, 2H), 3.8 (s, 3H), 6.65 (s, 1H), 7.2 (m, 4H), 7.35 (s, 1H), 7.5 (m, 1H), 8.7 (d, 1H), 8.8 (dd, 1H); mass spectrum (+ve ESP): 429 (M+H)+.

Provenance & Evidence