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

HRID 2063613Notes

Reaction equation

HRID 2063613 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][NH2:16])[CH:10]=1.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][N:16]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[CH3:17])[CH:10]=1

Participants

4

Reactant 2

HCID 750374-DimethylaminoacetophenoneHCID 60209698[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-hydrazine

Product 1

HCID 73320069[4-(1-{[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]dimethyl amineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-hydrazine (500 mg, 2.3 mmol) and 4-dimethylaminoacetophenone (380 mg, 2.3 mmol) were dissolved in 4 mL of ethanol. The resultant reaction mixture was heated in the microwave (CEM Discover, 135 C, QuickTest Method) for 3 hours. The reaction mixture was cooled to room temperature and after standing for three days yellow crystals formed. The crystalline solid was isolated by filtration and dried in vacuo to yield 580 mg (70%) of the title compound. HPLC Purity: 93%.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated in the microwave (CEM Discover, 135 C, QuickTest Method) for 3 hours
  3. customyellow crystals formed
  4. customThe crystalline solid was isolated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b903d7db47e04e34bdf80af338fc3373
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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