Potassium Carbonate → 5-bromo-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methyl-6-((6-methylpyridin-2-yl)methoxy)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-6-(6-methyl-pyridin-2-ylmethoxy)-3H-pyrimidin-4-one of Step D (54 mg, 0.12 mmol) in acetonitrile (1 mL) was added 2-hydroxy-2-methylpropionamidine HCl (25 mg, 0.18 mmol) and potassium carbonate (50 mg, 0.36 mmol) and the slurry was heated at 75° C. for eighteen hours. The reaction was returned to ambient temperature and filtered to remove excess salts. The filtrate was concentrated and purified via normal phase chromatography (ethyl acetate/heptane) to provide the title compound as a light yellow solid (27 mg, 42% yield). MS (M, M+2): 536, 538; 1H NMR (400 MHz, chloroform-d) δ ppm, 1.64 (s, 6H), 2.14 (s, 3H), 2.21 (s, 3H), 2.61 (s, 3H), 4.78 (s, 1H), 5.61-5.72 (m, 2H), 7.14 (d, J=7.83 Hz, 1H), 7.43 (d, J=7.44 Hz, 1H), 7.54-7.58 (m, 2H), 7.70 (s, 1H), 7.92 (s, 1H), 8.13 (d, J=7.82 Hz, 1H), 8.77 (d, J=5.09 Hz, 1H).

Provenance & Evidence