1,4-Cyclohexadiene → HCID 16063180, compound

HRID 1917259Notes

Reaction equation

HRID 1917259 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).

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-6a744ba44c7740769de060f12197f363
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

Loading…