Tetrabutylammonium Fluoride → N-(4-(6-((2-morpholinoethyl)carbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3-fluorophenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

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Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added cyclopropane-1,1-dicarboxylic acid {3-fluoro-4-[6-(2-morpholin-4-yl-ethylcarbamoyl)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-phenyl}-amide(4-fluoro-phenyl)-amide (0.049 g, 0.07 mmol, 1.0 eq.) and a 1M tetrabutylammonium fluoride solution (5 ml). The reaction was heated to reflux for 1 hour. The reaction was diluted with ethyl acetate, and was washed with (2×) H2O (50 ml), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash column chromatography using 3% methanol and DCM as the eluent, giving N-{3-fluoro-4-[(6-{[(2-morpholin-4-ylethyl)amino]carbonyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide as a white solid (0.014 g, 35% yield). 1H NMR (400 MHz, DMSO): 12.92 (s, 1H), 10.39 (bs, 1H), 10.36 (s, 1H), 10.04 (s, 1H), 9.11 (m, 1H), 8.37 (s, 1H), 7.83 (d, 1H), 7.66 (m, 2H), 7.46 (m, 1H), 7.40 (m, 1H), 7.15 (t, 2H), 3.98 (d, 2H), 3.77 (m, 3H), 3.56 (d, 2H), 3.16 (m, 2H), 3.02 (m, 3H), 1.59 (m, 2H), 1.36 (m, 2H); MS (ESI) for C30H29F2N7O5: 606 (MH+).

Provenance & Evidence