Diisopropylethylamine → 2-[2-(Isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

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Reaction Steps

To a 100 mL RBF, was added (R)-isopropyl-pyrrolidin-2-ylmethyl-amine (0.186 g, 0.86 mmol), and 50 mL dichloromethane at 0° C. under nitrogen. 0.3 mL diisopropylethylamine (1.71 mmol) was added drop wise, and stirred for 10 min. 2-Chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (0.2 g, 0.57 mmol) was added in one portion, and stirred at 0° C. to rt for 12 h. (This naphthyl chloro-intermediate was synthesized by a similar procedure as that of 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one.) The mixture was diluted with 100 mL dichloromethane, washed with sat. NaHCO3 and brine. After purified by flash chromatography, the title compound was obtained in 0.21 g as pale yellow solid. MS (ES+): 454 (M+H)+; (ES−): 452 (M−H).

Provenance & Evidence