4,6-Dichloro-n-methylpyrimidin-2-amine → 3-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 1585709Notes

Reaction equation

HRID 1585709 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[K+].[Cl:12][C:13]1[CH:14]=[C:15]([S:19]([NH-:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1>CN1CCCC1=O>[Cl:12][C:13]1[CH:14]=[C:15]([S:19]([NH:22][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=2)(=[O:20])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 1317213253-Chloro-benzenesulfonamide potassium salt

Product 1

HCID 193535593-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamideYield 53.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.24 g (0.00135 mol) of (4,6-dichloro-pyrimidin-2-yl)-methylamine and 0.62 g (0.0027 mol) of 3-chloro-benzenesulfonamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 150° C. for 8 hours. Then, the solvent was distilled off in a high vacuum, the residue was partitioned in ethyl acetate/water and extracted. The aqueous phase was made acid with 4N HCl and extracted with dichloromethane. The residue was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent. There was obtained 0.24 g (53%) of 3-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide as yellow crystals; m.p. 120-130° C. (dec.).

Workup

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. extractionextracted
  4. extractionextracted with dichloromethane
  5. customThe residue was chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent

Sources & evidence

ORD record
ord-39a0b1e99a3a4b0e981bc12d74687b3c
Source dataset
uspto-grants-1999_08
Patent number
US05939451

Reaction notes

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