Potassium Carbonate → N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyrimidin-4-yloxy)-4-methyl-benzamide

HRID 1028425Notes

Reaction equation

HRID 1028425 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([C:19]1[CH:20]=[C:21]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[C:22]([O:36][CH3:37])=[C:23]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([OH:34])[CH:28]=2)[CH:24]=1)([CH3:18])([CH3:17])[CH3:16]>C(#N)C.CN(C)C=O.O>[C:15]([C:19]1[CH:20]=[C:21]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[C:22]([O:36][CH3:37])=[C:23]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([O:34][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:28]=2)[CH:24]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-Dichloropyrimidine2×HCID 67217566N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide

Product 1

HCID 86664518N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyrimidin-4-yloxy)-4-methyl-benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

567 mg 2,4-dichloropyrimidine and 663 mg potassium carbonate are added to 1.50 g N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide in 15 ml acetonitrile and 3 ml N,N-dimethylformamide, and the reaction mixture is stirred overnight at ambient temperature. Then another 57 mg 2,4-dichloropyrimidine are added, and the mixture is stirred for a further hour at ambient temperature. For working up the reaction mixture is diluted with water and the white precipitate formed is filtered off, washed with water and dried in the desiccator.

Workup

  1. stirringthe mixture is stirred for a further hour at ambient temperature
  2. customthe white precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried in the desiccator

Sources & evidence

ORD record
ord-7cb204f5f0d445449d6e97f4edbe4e51
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

Loading…