2-adamantan-1-yl-N-(7-benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide → 2-adamantan-1-yl-N-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide

To a solution of 2-adamantan-1-yl-N-(7-benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin 4-yl)-acetamide in glacial acetic acid (15 mL) in a 250 ml round bottom flask was added 10% Pd/C (0.45 g). The resulting mixture was stirred for 15 h under an atmosphere of hydrogen (via a balloon), which was introduced after evacuation of air from the reaction vessel. The reaction was then filtered over celite, washed with EtOAc (20 mL) and the filtrate concentrated under reduced pressure. The residue was re-dissolved on EtOAc (50 mL) and stirred with aq. 10% NaOH solution (50 mL) for 1 h. The layers were separated and the aqueous layer washed with EtOAc (5×50 mL). The combined organics were dried over anhyd. Na2SO4, filtered and concentrated to yield 2-adamantan-1-yl-N-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide (0.68 g, 2.1 mmol, 87%) as a tan colored solid. LCMS (ESI+) m/z 327.3 [M+H]+

1. additionwas introduced after evacuation of air from the reaction vessel
2. filtrationThe reaction was then filtered over celite
3. washwashed with EtOAc (20 mL)
4. concentrationthe filtrate concentrated under reduced pressure
5. dissolutionThe residue was re-dissolved on EtOAc (50 mL)
6. stirringstirred with aq. 10% NaOH solution (50 mL) for 1 h
7. customThe layers were separated
8. washthe aqueous layer washed with EtOAc (5×50 mL)
9. customThe combined organics were dried over anhyd
10. filtrationNa2SO4, filtered
11. concentrationconcentrated

ORD record

ord-fa1de00822774f8186730e0bfa0d5b9f

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07297700B2