Water → 1-(1,3-dioxolan-2-ylmethyl)-1,6-naphthyridin-2(1H)-one

Temperature

55 °C

To a solution of 1.0 g of 1,6-naphthyridin-2(1H)-one in 10 mL of N,N-dimethylformamide, 0.30 g of 60% sodium hydride was added, and the mixture was stirred at 50 to 60° C. for 1 hour. Thereto was added 0.78 mL of 2-bromomethyl-1,3-dioxolan, and the reaction mixture was stirred at 90 to 100° C. for 30 minutes. Thereto were further added 0.30 g of 60% sodium hydride and 0.78 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 90 to 108° C. for 5 hours 30 minutes. The reaction mixture was cooled to room temperature, water and chloroform were then added thereto, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=100:1 to obtain 0.60 g of 1-(1,3-dioxolan-2-ylmethyl)-1,6-naphthyridin-2(1H)-one as a yellow solid.

1. stirringthe reaction mixture was stirred at 90 to 100° C. for 30 minutes
2. stirringthe mixture was stirred at 90 to 108° C. for 5 hours 30 minutes
3. temperatureThe reaction mixture was cooled to room temperature
4. customthe organic layer was separated
5. extractionthe aqueous layer was extracted with chloroform
6. washthe resultant solution washed with a saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationthe solvent was distilled off under reduced pressure
9. customThe resultant residue was purified by silica gel column chromatography

ORD record

ord-65d3b343df344eaabc3c7041a9ecfc5d

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367831B2