1,4-Cyclohexadiene → Diethyl-[4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-2-yl]-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of [7-benzyl-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-2-yl]-diethyl-amine (0.052 g, 0.13 mmol) in EtOH (1.5 mL) was added 10 wt % Pd/C and 1,4-cyclohexadiene (0.062 mL, 0.66 mmol). The mixture was heated at 85° C. for 2 h and cooled to rt. The mixture was concentrated and the residue was purified by FCC (2 M NH3/MeOH in CH2Cl2) to afford the title compound. HPLC: Rt=9.7 min. MS (ESI): mass calcd. for C17H21FN4, 300.4; m/z found, 301.4 [M+H]+. 1H NMR (CDCl3): 7.60 (dd, J=8.8, 5.5, 2H), 7.11 (t, J=8.8, 2H), 3.93 (s, 2H), 3.63 (q, J=7.0, 4H), 3.02 (t, J=5.7, 2H), 2.64 (t, J=5.7, 2H), 1.18 (t, J=7.0, 6H).

Provenance & Evidence