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

HRID 1844591Notes

Reaction equation

HRID 1844591 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-babe6643f9cf410f9b61338bf8809332
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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