1-(2-((2,5-Dichloropyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide → 1-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

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Reaction Steps

A suspension of 1-(2-((2,5-dichloropyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide (A13) (0.536 g, 1.61 mmol) and platinum oxide (0.110 g, 0.484 mmol) in DIPEA (16 mL) and MeOH (3 mL) was stirred under a hydrogen atmosphere for 58 hours. The resulting mixture was filtered through a pad of Celite and the filtrate concentrated in vacuo. The residue was diluted with water and EtOAc and filtered through a pad of Celite. The filtrate was extracted with EtOAc (2×20 mL) and the combined organic fractions were washed with water (3×20 mL), brine, dried (magnesium sulfate), filtered and concentrated in vacuo. The residue was adsorbed onto silica gel and purified by column chromatography (CombiFlash Rf, 24 g SiO2 Cartridge, 30-60% EtOAc in cyclohexane) to give the title compound A14 as a white solid (375 mg, 69%); 1H NMR (300 MHz, CDCl3) δ 8.52 (s, 1H), 7.43 (d, J=7.2 Hz, 1H), 7.28-7.31 (m, 3H), 5.37 (d, J=17 Hz, 2H), 3.27 (brs, 4H), 1.76 (brs, 2H), 1.16 (brs, 2H). LCMS-B: rt 5.30 min; m/z 337 [M+H]+.

Provenance & Evidence