Water → 2-[5-Bromo-2-(2,4-dimethoxy-phenylamino)-pyrimidin-4-ylamino]-N-methyl-benzenesulfonamide

HRID 2382632Notes

Reaction equation

HRID 2382632 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH:19][CH3:20])(=[O:18])=[O:17])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:21][O:22][C:23]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:24]=1[NH2:25].O>C(O)C.Cl>[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH:19][CH3:20])(=[O:18])=[O:17])=[N:4][C:5]([NH:25][C:24]2[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:23]=2[O:22][CH3:21])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 176522,4-DimethoxyanilineHCID 587483992-(5-bromo-2-chloro-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide

Product 1

HCID 454826262-[5-Bromo-2-(2,4-dimethoxy-phenylamino)-pyrimidin-4-ylamino]-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide (300 mg, 0.79 mmol), 2,4-dimethoxyaniline (181.5 mg, 1.18 mmol) in ethanol (3 mL), 1 N hydrochloric acid (0.03 mL) is added and stirred under reflux condition for 5 hours. The reaction mixture is cooled to room temperature, poured into water and extracted twice with ethyl acetate. The organic layer is successively washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 1:1) to afford the title compound.

Workup

  1. temperatureunder reflux condition for 5 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer is successively washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 1:1)

Sources & evidence

ORD record
ord-ff307c7204eb4baaad43fe840e22219f
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

Loading…