4-Dimethylaminoacetophenone → Dimethyl-(4-{1-[(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]ethyl}-phenyl)amine

HRID 2063601Notes

Reaction equation

HRID 2063601 reaction equation
Cl.Cl.Cl.[NH:4]([C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]=[C:8]([CH3:18])[N:7]=1)[NH2:5].C(N(C(C)C)CC)(C)C.[CH3:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=1)=O>C(O)C>[CH3:38][N:37]([CH3:39])[C:34]1[CH:35]=[CH:36][C:31]([C:29](=[N:5][NH:4][C:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]=[C:8]([CH3:18])[N:7]=2)[CH3:28])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 750374-DimethylaminoacetophenoneHCID 81531DiisopropylethylamineHCID 602096944-Hydrazino-2-methyl-6-phenylpyrimidine trihydrochloride

Product 1

HCID 72577515Dimethyl-(4-{1-[(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]ethyl}-phenyl)amineYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydrazino-2-methyl-6-phenylpyrimidine trihydrochloride (300 mg, 0.97 mmol) and diisopropylethylamine (0.17 mL, 0.97 mmol) in ethanol (10 mL) was added 4-dimethylaminoacetophenone (158 mg, 0.97 mmol). The resultant reaction mixture was heated at reflux overnight. The reaction mixture was diluted with dIH2O and the pH was adjusted to 1-2 and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 9-10 and was extracted with ethyl acetate. The combined extracts were concentrated in vacuo and the residue crystallized from ethyl acetate:hexanes. 60 mg (18%) of the title compound was isolated as a yellow solid. HPLC Purity: 98%.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. additionThe reaction mixture was diluted with dIH2O
  5. washwashed with ethyl acetate
  6. extractionwas extracted with ethyl acetate
  7. concentrationThe combined extracts were concentrated in vacuo
  8. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fbad22d60b474785afdfbc0007cc2d89
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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