Acetic Acid → 5,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

To a solution of sodium methoxide (1.67 g, 30.9 mmol) in anhydrous MeOH (10 mL) at room temperature was added formamidine acetate (1.15 g, 11 mmol) in one portion as solid followed by ethyl-1-benzyl-3-oxo-4-piperidine carboxylate hydrochloride (2.63 g, 8.83 mmol) in one portion. The reaction mixture was stirred at rt for 20 h. The reaction was cooled at 0° C., and water (6 mL) was added followed by acetic acid (0.63 mL, 11 mmol) and the mixture was stirred at rt for 1 h. The mixture was concentrated under vacuum to remove the methanol and then stirred at rt overnight. The resulting solid was collected by filtration and washed with water (5 mL×3) and dried on filter to afford the title compound a (1.50 g, 70%) as an orange solid. LCMS [M+H]+ 242.16.

1. temperatureThe reaction was cooled at 0° C.
2. stirringthe mixture was stirred at rt for 1 h
3. concentrationThe mixture was concentrated under vacuum
4. customto remove the methanol
5. stirringstirred at rt overnight
6. filtrationThe resulting solid was collected by filtration
7. washwashed with water (5 mL×3)
8. customdried
9. filtrationon filter

ORD record

ord-3f094f4a96004692ba80b139fbe2cfec

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309571B2