Hydrochloric Acid → HCID 53353334, compound

HRID 451407Notes

Reaction equation

HRID 451407 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:16].Cl.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.Cl>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[ClH:15].[ClH:16].[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[CH2:23][CH2:24]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 446300684-(4-AMINOPIPERIDINO)PYRIDINE DIHYDROCHLORIDEHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 53353334HCID 53353334, compound

Reagents, catalysts & solvents 3

HCID 312751,4-DioxaneCatalystHCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 4-benzyl-2-chloro-6-methyl-pyrimidine (WO2009103652; 70 mg, 0.32 mmol) and 4-(4-aminopiperidino)pyridine dihydrochloride (ABCR; 80 mg, 0.32 mmol) in dioxane (2 mL) was added potassium carbonate (885 mg, 6.4 mmol), palladium(II) acetate (3 mg, 0.013 mmol) and 2-(dicyclohexylphosphino)biphenyl (11 mg, 0.031 mmol). The reaction mixture was refluxed overnight, concentrated, hydrolyzed and extracted with ethyl acetate. Chromatography on Si-Amine (Silicycle, 10 g) using cyclohexane/ethyl acetate as eluent gave a gummy solid which was dissolved in dioxane and treated with a few drops of dioxane saturated with HCl gas to yield the title compound as a slightly yellow solid (70 mg, 51%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated
  3. extractionhydrolyzed and extracted with ethyl acetate
  4. customgave a gummy solid which

Sources & evidence

ORD record
ord-273ca30457074b748f0ed60443dd408e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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