Toluene → 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

HRID 1082265

Reaction equation

HRID 1082265 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH2:18])[C:13]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=N[CH:7]=1.[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27].[OH-].[K+].[C:43]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:18][C:14]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[CH:43]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=3)[N:17]=[CH:16][N:15]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 117291026-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amineHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

Product 1

HCID 196894884-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-b065fb797d834479958f8737ac1e6783
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Linked notes

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