Ethyl Acetate → HCID 68408299, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of N-(2-t-butoxycarbonylaminophenyl)-4-[2-(methylthio)thieno[3,2-d]pyrimidin-4-yl]benzamide (Method 55, 960 mg, 1.95 mg) in DMF (40 ml), was added meta-chloroperbenzoic acid (57%, 630 mg, 2.08 mmol) and the reaction mixture stirred, allowing warming to ambient temperature. After 3 hours a further portion of meta-chloroperbenzoic acid (70%, 589 mg, 2.40 mmol) was added and stirring continued for 2 hours. The reaction mixture was then carefully poured into aqueous sodium metabisulfite solution (0.25M, 100 ml), before addition of ethyl acetate (100 ml). The insoluble material was removed by filtration and dried in vacuo to yield the title compound (586 mg, 57%); NMR Spectrum: (DMSO-d6) 1.46 (s, 9H), 3.57 (s, 3H), 7.18 (t, 1H), 7.24 (t, 1H), 7.59 (m, 2H), 8.00 (d, 1H), 8.27 (d, 2H), 8.41 (d, 2H), 8.75 (s, 1H), 8.90 (d, 1H), 10.07 (s, 1H); Mass Spectrum: M+Na+ 547.

Provenance & Evidence