2-Amino-4,6-dichloropyrimidine → N-[4-(2-amino-6-chloropyrimidin-4-ylsulfamoyl)phenyl]-acetamide

HRID 378259Notes

Reaction equation

HRID 378259 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[K].[S:11]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=1)(=[O:14])(=[O:13])[NH2:12]>CN1CCCC1=O>[NH2:1][C:2]1[N:3]=[C:4]([NH:12][S:11]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=2)(=[O:13])=[O:14])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 70262342N-(4-sulfamoyl-phenyl)-acetamide potassium salt

Product 1

HCID 10736032N-[4-(2-amino-6-chloropyrimidin-4-ylsulfamoyl)phenyl]-acetamideYield 67%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.98 g (0.006 mol) of 2-amino-4,6-dichloropyrimidine and 3.03 g (0.012 mol) of N-(4-sulfamoyl-phenyl)-acetamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 140° C. for 8 hours. Then, the solvent was distilled off in a high vacuum, the residue was partitioned in ethyl acetate/water, the inorganic phase was saturated with sodium chloride and the remaining ethyl acetate dissolved in the aqueous was distilled off on a rotary evaporator. The aqueous phase was made acid with 1N HCl, the crystals which separated were filtered off under section and washed with water. After drying there were obtained 1.37 g (67%) of N-[4-(2-amino-6-chloro-pyrimidin-4-yisulfamoyl)-phenyl]-acetamide as beige crystals; m.p.: 272-273° C. (dec.).

Workup

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. dissolutionthe remaining ethyl acetate dissolved in the
  4. distillationaqueous was distilled off on a rotary evaporator
  5. customthe crystals which separated
  6. filtrationwere filtered off under section
  7. washwashed with water
  8. customAfter drying there

Sources & evidence

ORD record
ord-4d91208e308344d3a94dad2abb1e8736
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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