Tetrahydrofuran → HCID 69507344, compound

Participants

Reaction Steps

Methylmagnesium iodide (3M solution in tetrahydrofuran, 5.6 mL, 16.9 mmol, 1.5 eq) was added dropwise over 10 minutes to a chilled (0°) solution of 4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-N-methoxy-N-methylbutanamide (4.0 g, 11.25 mmol, 1 eq) in tetrahydrofuran (THF) (50 mL). The reaction mixture was stirred at ambient temperature for 4 hours, quenched with 1 M hydrochloric acid, and concentrated under reduced pressure. The residue was diluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was extracted with dichloromethane (2×30 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to produce 3.12 g of 5-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one as a tan solid.

Provenance & Evidence