HCID 86624862, compound → [4-(1-{[6-(2-Amino-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine

HRID 2063603Notes

Reaction equation

HRID 2063603 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[C:18]([NH:20][N:21]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[CH3:23])[N:17]=[C:16]([CH3:33])[N:15]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:15]=[C:16]([CH3:33])[N:17]=[C:18]([NH:20][N:21]=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([N:30]([CH3:32])[CH3:31])=[CH:28][CH:29]=2)[CH3:23])[CH:19]=1

Participants

4

Reactant 1

HCID 86624862HCID 86624862, compound

Product 1

HCID 73320052[4-(1-{[6-(2-Amino-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamineYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-(6-{N′-[1-(4-dimethylamino-phenyl)-ethylidene]-hydrazino}-2-methyl-pyrimidin-4-yl)-phenyl]-carbamic acid tert-butyl ester was dissolved in 10 mL of 5% trifluoroacetic acid in dichloromethane. The resultant reaction mixture was stirred at room temperature for 2 hours before being concentrated in vacuo. The residue was dissolved in methanol and the pH was adjusted to 7 with potassium bicarbonate. After filtration the methanol was concentrated in vacuo and the residue was purified by Si gel chromatography (1:1 ethyl acetate:hexanes) yielding 140 mg (60%) of the title compound as a brown solid. HPLC Purity: 95%.

Workup

  1. customThe resultant reaction mixture
  2. concentrationbefore being concentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol
  4. filtrationAfter filtration the methanol
  5. concentrationwas concentrated in vacuo
  6. customthe residue was purified by Si gel chromatography (1:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-56a5c2c2ff0a4ec68e18b0ac24b60a70
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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