Dimethylformamide → 4-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

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Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 4-chloro-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.178 g, 0.39 mmol, 1.0 eq.), 1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarboxylic acid (0.133 g, 0.59 mmol, 1.5 eq), HATU (0.379 g, 0.98 mmol, 2.5 eq), TEA (0.17 ml, 1.17 mmol, 3 eq), and dry DMF (5 ml). The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with (2×) H2O (50 ml), sat'd NaHCO3 (2×), 5% LiCl (3×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo, giving 4-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a cream solid (0.138 g, 53% yield). MS (ESI) for C32H35F2N5O6Si: 517 (MH+).

Provenance & Evidence