Sodium hydride → HCID 68160028, compound

Participants

Reaction Steps

To a slurry of sodium hydride (60 wt % in mineral oil, 0.04 g, 1.0 mmol) in N,N-dimethylformamide (2 ml) under nitrogen atmosphere was added (S)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol (0.13 g, 0.70 mmol) in N,N-dimethylformamide (1 ml) at room temperature. The resulting mixture was stirred for 15 minutes. To the mixture was added 2-chloro-6-(3-fluoro-pyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.14 g, 0.60 mmol) at room temperature. After the mixture was stirred for 3 hours, the reaction was quenched with water and partitioned between water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 0/100) to afford 6-(3-fluoro-pyridin-4-yl)-3-methyl-2-[(3S)-1-thiophen-3-yl-pyrrolidin-3-ylmethoxy]-3H-pyrimidin-4-one (0.045 g, 0.12 mmol, 19%) as a yellow solid.

Provenance & Evidence