HCID 18989386, compound → HCID 18989408, compound

HRID 2395623Notes

Reaction equation

HRID 2395623 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]([CH3:22])[C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[N:9]=[C:8]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>C(O)(=O)C.[Pt]=O>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([N:12]([C:10]2[N:11]=[C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[N:7]=[C:8]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:9]=2)[CH3:22])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 18989386HCID 18989386, compound

Product 1

HCID 18989408HCID 18989408, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

2-(1-Imidazolyl)-4-[N-methyl-N-(4-nitrophenyl)amino]-6-morpholino-1,3,5-triazine (115 mg, 0.30 mmol) was dissolved in acetic acid (10 ml) and was catalytically reduced with platinum oxide at room temperature under normal pressure. The reaction mixture was filtered and was evaporated under reduced pressure. The obtained residue was added with dichloromethane and aqueous solution of saturated sodium bicarbonate, and then was shaken for mixing. The organic layer was separated from the mixture, washed with water, dried over anhydrous magnesium sulfate and evaporated. The obtained residue was purified by silica gel column chromatography, using ethyl acetate as eluant, to obtain 36.5 mg (yield: 34.4%) of the titled compound as colorless crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customwas evaporated under reduced pressure
  3. additionThe obtained residue was added with dichloromethane and aqueous solution of saturated sodium bicarbonate
  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. customevaporated
  9. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f893db643fa9416a90d16d9bb0e58871
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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