Potassium Carbonate → 3-{3-[2-Fluoro-6-(4-methoxy-benzylamino)-pyridin-4-ylmethyl]-5-isopropenyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile

Participants

Reaction Steps

A solution of 3-(5-isopropenyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (0.0375 g, 0.127 mmol), methanesulfonic acid 2-fluoro-6-(4-methoxy-benzylamino)-pyridin-4-ylmethyl ester (0.024 g, 0.072 mmol), lithium iodide (0.0048 g, 0.036 mmol) and potassium carbonate (0.010 g, 0.072 mmol) in DMF (1.0 mL) was stirred at 0° C. for 2 h, then warmed to rt. After 6 h, reaction mixture was diluted with ethyl acetate, washed with water (2×), dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane) to give a yellow solid (0.019 g, 49%). 1H NMR (300 MHz, CD3CN): δ 7.87 (s, 1H), 7.74 (s, 1H), 7.65 (s, 1H), 7.19 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 5.89 (s, 1H), 5.84 (s, 1H), 5.66 (br s, 1H), 5.2-4.95 (br s, 1 h), 4.92 (s, 1H), 4.70 (s, 1H), 4.5-4.2 (br s, 1H), 4.20 (d, J=5.7 Hz, 2H), 3.75 (s, 3H), 2.30 (s, 3H), 1.67 (s, 3H). Mass spectrum: 538.1 (M+H)+.

Provenance & Evidence