Methanol → HCID 67883923, compound

Participants

Reaction Steps

To a solution of 2-[5-(4-nitrobenzylaminosulfonylamino)-6-oxo-2-thienyl-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.431 g) in acetic acid (12 mL) was added acetic anhydride (0.265 mL), followed by iron powder (0.783 g). The reaction was stirred at room temperature overnight. Methanol was added and the reaction mixture filtered through diatomaceous earth to remove excess iron. Ethyl acetate was added and the resultant solution washed (water (twice), brine), dried (MgSO4) and evaporated. The crude material was purified by chromatography, with dichloromethane:methanol (gradient, 99.5:0.5, 98:2) as the eluent, to provide the title compound (0.247 g); TLC: Rf =0.27, dichloromethane:methanol (98:2); NMR: 0.87-0.97 (m,6), 2.17-2.30 (m,1), 3.32 (s,3), 4.02 (d,2), 4.73-4.77 (m,1) 4.77-4.93 (m,2), 7.13-7.20 (m,3), 7.33 (d,1), 7.47 (d,2), 7.80-7.87 (m,1), 7.91 (s,1), 7.97-8.03 (m,1), 9.04 (d,1), 9.09 (s,1), 9.87 (s,1); MS: m/z=629(M+1).

Provenance & Evidence