Potassium Carbonate → HCID 59278668, compound

HRID 1942908Notes

Reaction equation

HRID 1942908 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]3)=[C:11]([O:21][CH3:22])[CH:10]=2)[N:5]=[C:4]([N:23]([CH3:25])[CH3:24])[N:3]=1.[OH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]([F:36])([F:35])[F:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:22][O:21][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:5]=[C:4]([N:23]([CH3:25])[CH3:24])[N:3]=[C:2]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:34])([F:35])[F:36])[N:7]=2)[CH:14]=[CH:13][C:12]=1[N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 679582-TrifluoromethylphenolHCID 59278672HCID 59278672, compound

Product 1

HCID 59278668HCID 59278668, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

6-Chloro-N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-N′,N′-dimethyl-[1,3,5]triazine-2,4-diamine (200 mg, 0.56 mmol) in 7 ml acetonitrile was treated with 2-hydroxy-benzotrifluoride (95 mg, 0.59 mmol) and potassium carbonate (85 mg, 0.62 mmol). The resulting mixture was stirred under reflux for 5 days. The mixture was then diluted with 25 ml of water and extracted with ethyl acetate. Chromatography on silica gel using ethyl acetate as a solvent and subsequent crystallization from methanol gave the title compound as colorless solid (42 mg, 16%).

Workup

  1. temperatureunder reflux for 5 days
  2. extractionextracted with ethyl acetate
  3. customsubsequent crystallization from methanol

Sources & evidence

ORD record
ord-9a0a47bab810467fa336a727afa2d753
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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