Ethanol → HCID 20183309, compound

HRID 255731Notes

Reaction equation

HRID 255731 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([NH2:25])=[O:24].C=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[CH2:35](O)C>ClCCCl>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([NH:25][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1)=[O:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 11724425HCID 11724425, compound

Product 1

HCID 20183309HCID 20183309, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide (5 g), formalin (37%, 1.35 ml), N-methylpiperazine (2.25 g), ethanol (50 ml) and 1,2-dichloroethane (25 ml) was refluxed for 6 hours. After evaporating the solvent in vacuo, the residue was chromatographed on alumina (200 ml) and eluted 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-N-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxamide (1.90 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAfter evaporating the solvent in vacuo
  3. customthe residue was chromatographed on alumina (200 ml)
  4. washeluted with chloroform
  5. additionThe fractions containing the object compound
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-002b837b81614d6783b6c08f9450c410
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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