1-Methylpiperazine → 6-Methyl-5-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4683Notes

Reaction equation

HRID 4683 reaction equation
Br[CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[N:5][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:8]=1[CH3:9].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(O)(C)C>[CH3:9][C:8]1[N:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:3]=1[CH2:2][N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 104300785-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 100241216-Methyl-5-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-bromomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g), N-methylpiperazine (1.17 g) in isopropyl alcohol (15 ml) was refluxed for 6 hours. After evaporating the solvent, the residue was dissolved in chloroform, washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The filtrate was evaporated under reduced pressure, and the residue was subjected to column chromatography on alumina (100 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 6-methyl-5-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine. (0.30 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAfter evaporating the solvent
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe filtrate was evaporated under reduced pressure
  7. washeluting with chloroform
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-f9e672f1e9b44c4186cfbb5036d7a208
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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