Pyridine → N-(4-tert-Butylphenyl)-1-(pyrimidin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

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Reaction Steps

To a suspension of 1-Pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid (60.4 mg, 0.194 mmol) and DMF (cat) in CH2Cl2 (1 mL) was added (COCl)2 (0.027 mL, 0.31 mmol). The mixture was stirred for 90 minutes, diluted with PhMe (0.5 mL), concentrated under reduced pressure to dryness, and dissolved in CH2Cl2 (1.5 mL). To the solution were added pyridine (0.027 mL, 0.33 mmol), DMAP (cat), and 4-tert-butylaniline (0.037 mL, 0.023 mmol). The mixture was stirred 1 hour, diluted with water and extracted with CH2Cl2, dried (Na2SO4), and purified by flash chromatography (7% EtOAc/CH2Cl2) to provide 1-Pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid (4-tert-butyl-phenyl)-amide as a white solid (54.2 mg, 0.123 mmol, 63%): MS (ESI+) m/z 337 (M+H)+, m/z 334 (M−H)−; 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.31 (s, 9 H), 2.59 (m, 2 H), 4.04 (t, J=5.6 Hz, 2 H), 4.44 (q, J=3.1 Hz, 2 H), 6.54 (t, J=4.7 Hz, 1 H), 6.75 (m, 1 H), 7.36 (m, 3 H), 7.47 (m, 2 H), 8.35 (d, J=4.7 Hz, 2 H).

Provenance & Evidence