Water → 5-[5-Amino-6-[2-(3-hydroxyphenyl)ethynyl]pyrazin-2-yl]-1-isopropyl-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

3-[2-(3-Amino-6-bromo-pyrazin-2-yl)ethynyl]phenol (100 mg, 0.3447 mmol), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (108.8 mg, 0.4136 mmol) and K3PO4 (146.3 mg, 0.6894 mmol) were combined in MeCN (2 mL)/water (0.5 mL) and Pd[P(tBu)3]2 (8.811 mg, 0.01724 mmol) was added. The reaction was heated at 60° C. for 15 hours. The reaction was cooled to ambient temperature and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (VARIAN 971-FP™, 8 g column, eluting with 0 to 10% MeOH/DCM, dry loaded) to give the title compound as a yellow solid (25.2 mg, 21% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.38 (d, 6H), 5.11 (sept, 1H), 6.49 (d, 1H), 6.77 (s, 2H), 6.87 (dd, 1H), 7.12 (s, 1H), 7.18 (d, 1H), 7.25 (t, 1H), 7.99 (dd, 1H), 8.20 (d, 1H), 8.55 (s, 1H) and 9.74 (s, 1H) ppm; MS (ES+) 347.1.

Provenance & Evidence