Ethanol → HCID 25070908, compound

HRID 2077036Notes

Reaction equation

HRID 2077036 reaction equation
CC1CC=CCC=1.C([N:15]1[CH2:21][CH2:20][C:19]2[C:22](Cl)=[N:23][C:24]([CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:27])=[N:25][C:18]=2[CH2:17][CH2:16]1)C1C=CC=CC=1.[CH2:35]([OH:37])[CH3:36]>[OH-].[Pd+2].[OH-]>[CH2:35]([O:37][C:22]1[C:19]2[CH2:20][CH2:21][NH:15][CH2:16][CH2:17][C:18]=2[N:25]=[C:24]([CH:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:27])[N:23]=1)[CH3:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 780061-Methyl-1,4-cyclohexadieneHCID 59312363HCID 59312363, compound

Product 1

HCID 25070908HCID 25070908, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Palladium hydroxide (20% on carbon) (43 mg, 0.3 mmol) and 1-methyl-1,4-cyclohexadiene (3.42 ml, 30.5 mmol) was added to a solution of 7-benzyl-4-chloro-2-(1-phenylethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine of preparation 30, Step B, (1.15 g, 3.04 mmol) in ethanol (30 ml) and refluxed, under nitrogen, for 16 h. The reaction mixture was filtered through Arbocel then the filtrate was concentrated in vacuo. The residue was purified by column chromatography on Biotage 40S cartridge, eluting with DCM:MeOH (100:0 to 90:10), to afford the title compound as a solid in 69% yield, 629 mg.

Workup

  1. temperaturerefluxed, under nitrogen, for 16 h
  2. filtrationThe reaction mixture was filtered through Arbocel
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography on Biotage 40S cartridge
  5. washeluting with DCM:MeOH (100:0 to 90:10)

Sources & evidence

ORD record
ord-a162dfa0a3db45ee944a1830c6763750
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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