Monoperoxyphthalic Acid Magnesium Salt → HCID 59726837, compound

Participants

Reaction Steps

1-(2,4-Difluoro-benzyl)-6-[5-(6-ethoxy-2-methylsulfanyl-pyrimidin-4-yl)-thiophen-2-yl]-2-oxo-4-trifluoromethyl-1,2-dihydropyridine-3-carbonitrile (49 mg, 0.087 mmol) was dissolved in a mixture of dichloromethane (2 mL) and methanol (0.4 mL). To this solution was added magnesium monoperoxyphthalate hexahydrate, MMPP, (108 mg, 0.218 mmol, 80% tech.) and the mixture was stirred at ambient temperature for overnight. After this period the reaction mixture was combined with dichloromethene (20 mL) and was washed with 1M NaHCO3 (2×10 mL), and brine (10 mL). The resulting organic layer was separated and dried over anhydrous Na2SO4 and evaporated in vacuo to yield crude product. The crude product was purified using flash silica chromatography (25-50% EtOAc/Hexane) to yield 1-(2,4-difluorobenzyl)-6-[5-(6-ethoxy-2-methanesulfonyl-pyrimidin-4-yl)-thiophen-2-yl]-2-oxo-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile (42 mg, 80%) as a yellow solid. 1H-NMR (CDCl3): δ 7.72 (m, 1 H), 7.14 (m, 1 H), 7.13 (m, 1 H), 7.07 (s, 1 H), 6.88 (m, 1 H), 6.78 (m, 1 H), 6.63 (s, 1 H), 5.40 (s, 2 H), 4.61 (q, J=7.1 Hz, 2 H), 3.36 (s, 3 H), 1.46 (t, J=7.1 Hz, 3 H). MS(ES+): 597.2 (M+H).

Provenance & Evidence