Water → 2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-N-propyl-benzenesulfonamide

HRID 2382634Notes

Reaction equation

HRID 2382634 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH:20][CH2:21][CH2:22][CH3:23])(=[O:19])=[O:18].[H-].[Na+].O>CS(C)=O>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([NH:20][CH2:21][CH2:22][CH3:23])(=[O:19])=[O:18])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 47136732-amino-N-propylbenzenesulfonamide

Product 1

HCID 866088272-(5-bromo-2-chloro-pyrimidin-4-ylamino)-N-propyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer is washed with water
  3. dry with materialbrine, dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f4247d7e0bf543c296f1419ac637443d
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

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