Dimethylformamide → 5-(1-Imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4687Notes

Reaction equation

HRID 4687 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[CH2:23][NH:24][C:25]([NH2:27])=S.[CH3:28]I.C[N:31]([CH3:34])C=O>>[N:31]1[CH2:34][CH2:28][NH:27][C:25]=1[NH:24][CH2:23][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[N:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 201513886-Methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine

Product 1

HCID 201514185-(1-Imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Procedure

A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine (0.7 g) and methyl iodide (0.31 g) in N,N-dimethylformamide (20 ml) was stirred for 7 hours at a room temperature. After evaporating the solvent in vacuo, the residual product was dissolved in ethanol (14 ml). Ethylenediamine (0.33 g) was added thereto and refluxed for 2 hours. After cooling, the reaction mixture was poured into a mixture of chloroform (50 ml) and water (100 ml), and adjusted pH to 11.0 with 10% aqueous potassium carbonate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, evaporated in vacuo. The residual product was subjected to column chromatography on alumina eluting with a mixture of chloroform and methanol (50:1). The fractions containing the object compound were combined and concentrated in vacuo. The residue was recrystallized from ethanol to give 5-(1-imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.06 g).

Workup

  1. customAfter evaporating the solvent in vacuo
  2. dissolutionthe residual product was dissolved in ethanol (14 ml)
  3. additionEthylenediamine (0.33 g) was added
  4. temperaturerefluxed for 2 hours
  5. temperatureAfter cooling
  6. additionthe reaction mixture was poured into a mixture of chloroform (50 ml) and water (100 ml)
  7. customThe organic layer was separated
  8. washwashed with saturated aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. additionThe residual product was subjected to column chromatography on alumina eluting with a mixture of chloroform and methanol (50:1)
  12. additionThe fractions containing the object compound
  13. concentrationconcentrated in vacuo
  14. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ef17da84c683468391c7243b8c369f7e
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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