Potassium Carbonate → 2-{(2S)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-morpholin-4-yl}-1H-[4,4']bipyrimidinyl-6-one

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Reaction Steps

To a solution of (2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)morpholine hydrochloride (intermediate 13, 4.00 g, 14.2 mmol) and 1H-pyrazole-1-carboxamidine hydrochloride (2.19 g, 14.9 mmol) in N,N-dimethylformamide (14 ml) was added. N,N-diisopropylethylamine (4.05 g, 31.3 mmol) at room temperature and the solution was stirred for 4 hours. The solution was decanted with ether, then 3-oxo-3-pyrimidin-4-yl-propionic acid ethyl ester (3.59 g, 18.5 mmol), potassium carbonate (4.92 g, 35.6 mmol) and ethanol (30 ml) were added to the resulting solution. After refluxed for 18 hours, the solution was concentrated under reduced pressure. The residue was washed with water and the hot mixture of ethanol and 1N hydrochloric acid (1/1, v/v), and dried under reduced pressure to afford 2-{(2S)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-morpholin-4-yl}-1H-[4,4′]bipyrimidinyl-6-one (1.94 g, 33%).

Provenance & Evidence