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

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-6-(2-methyl-thiazol-4-ylmethoxy)-3H-pyrimidin-4-one from Step C (87 mg, 0.21 mmol) in acetonitrile (2 mL) was added 2-hydroxy-2-methylpropionamidine HCl (44 mg, 0.32 mmol) and potassium carbonate (87 mg, 0.63 mmol) and the slurry was heated at 75° C. for two hours and at ambient temperature for eighteen hours. The reaction was 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 white solid (12 mg, 11% yield). MS (M+H): 499; 1H NMR (400 MHz, chloroform-d) δ ppm, 1.64 (s, 6H), 2.17 (s, 3H), 2.21 (s, 3H), 2.77 (s, 3H), 5.59-5.68 (m, 2H), 7.26 (s, 1H), 7.55-7.59 (m, 2H), 7.93 (s, 1H), 8.14 (d, J=8.60, 1H), 8.78 (d, J=5.08, 1H).

Provenance & Evidence