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

HRID 2424369Notes

Reaction equation

HRID 2424369 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-d59e96f24b8c43a497481865c42c8a7a
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

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