Piperazine → 3,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4328

Reaction equation

HRID 4328 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[N:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[N:3]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:4]2[N:3]=[C:2]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:7]([CH3:8])[C:6](=[N:9][C:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[CH3:18])[CH:5]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 201522932-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

Product 1

HCID 201523163,4-Dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidineYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.07 g) in ethanol (10 ml) was added piperazine (0.70 g). The mixture was refluxed for 3 hours, cooled to ambient temperature. The mixture was evaporated, and the residue was dissolved in chloroform and washed with aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel using a mixture of chloroform and methanol (95:5) to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine (0.69 g).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel using
  8. additiona mixture of chloroform and methanol (95:5)

Sources & evidence

ORD record
ord-dc411ea16f934b7bbc3fdf11d0029adc
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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