1,4-Cyclohexadiene → HCID 16063180, compound

HRID 1817704Notes

Reaction equation

HRID 1817704 reaction equation
[ClH:1].[CH2:2]([C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:12]2[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][C:13]=2[N:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1CC=CCC=1>CCO.[Pd]>[ClH:1].[CH2:2]([C:9]1[N:10]=[C:11]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[C:12]2[CH2:18][CH2:17][NH:16][CH2:15][C:13]=2[N:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 16063048HCID 16063048, compound

Product 1

HCID 16063180HCID 16063180, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2,7-dibenzyl-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine hydrochloride in EtOH was added 10% Pd/C (1 equiv) followed by 1,4-cyclohexadiene (5 equiv). The mixture was heated at 85° C. for 5 h, filtered and concentrated. The residue was dissolved in CH2Cl2 and treated with Dowex 550A resin. After 1 h, the resin was removed by filtration and the filtrate was concentrated. Chromatography on SiO2 (2 M NH3 in MeOH/CH2Cl2) afforded the title compound. MS (ESI): exact mass calcd. for C20H18FN3, 319.15; m/z found, 320.4 [M+H]+. 1H NMR (MeOH-d4): 7.70-7.67 (m, 2H), 7.36-7.35 (m, 2H), 7.31-7.25 (m, 4H), 7.20-7.17 (m, 1H), 4.42 (s, 2H), 4.26 (s, 2H), 3.48 (t, J=6.1, 2H), 3.09 (t, J=6.1, 2H). The compounds in Examples 77-81 were prepared using methods similar to those described in Example 76.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. additiontreated with Dowex 550A resin
  5. customthe resin was removed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-01232a0f327948498c21f86b0c36de1b
Source dataset
uspto-grants-2009_10
Patent number
US07598255B2

Reaction notes

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