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

HRID 72798Notes

Reaction equation

HRID 72798 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:13][C:12]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[N:11][C:10]=2[CH2:9]1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[Pd]>[CH2:28]([N:25]([CH2:26][CH3:27])[C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:15]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[N:11]=1)[CH3:29]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 46206188[7-Benzyl-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-2-yl]-diethyl-amine

Product 1

HCID 46206189Diethyl-[4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-2-yl]-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  1. temperaturecooled to rt
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by FCC (2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b00f33ee539c4c73bce186cdb205feee
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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