Imidazole → 4-(1H-imidazol-1-yl)-N-methyl-6-(morpholin-4-yl)-N-phenyl-1,3,5-triazin-2-amine

HRID 2395615Notes

Reaction equation

HRID 2395615 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:3]=1.[OH-].[Na+].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>CN(C=O)C>[N:24]1([C:2]2[N:7]=[C:6]([N:8]([CH3:15])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:5]=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:3]=2)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 108284402-chloro-4-(N-methyl-N-phenylamino)-6-morpholino-1,3,5-triazine

Product 1

HCID 6677074-(1H-imidazol-1-yl)-N-methyl-6-(morpholin-4-yl)-N-phenyl-1,3,5-triazin-2-amineYield 52.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The obtained 2-chloro-4-(N-methyl-N-phenylamino)-6-morpholino-1,3,5-triazine (135 mg, 0.457 mmol) was dissolved in DMF (5 ml), added with sodium hydroxide (19.2 mg, 0.480 mmol) and imidazole (32.7 mg, 0.480 mmol) and stirred at 110° C.-120° C. for 5 hours. After allowing to cool to room temperature, the solvent was removed under reduced pressure. The residue was added with ethyl acetate and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography, using dichloromethane and methanol (20:1) as eluant, to obtain 71.3 mg (yield: 52.8%) of the titled compound as colorless crystals.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was added with ethyl acetate and water
  3. stirringshaken
  4. additionfor mixing
  5. customThe organic layer was separated from the mixture
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c67816be3c4f4b609c8a3f134d14aed4
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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