4,6-Dichloro-n-methylpyrimidin-2-amine → HCID 17774521, compound

HRID 378292Notes

Reaction equation

HRID 378292 reaction equation
[K+].[C:2]1([S:8]([NH-:11])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][NH:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[C:16]([Cl:21])[N:15]=1>CN1CCCC1=O.[OH-].[Na+]>[CH3:12][NH:13][C:14]1[N:19]=[C:18]([NH:11][S:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:10])=[O:9])[CH:17]=[C:16]([Cl:21])[N:15]=1

Participants

5

Reactant 2

HCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 12228336HCID 12228336, compound

Product 1

HCID 17774521HCID 17774521, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

5.38 g (0.0275 mol) of benzenesulfonamide potassium salt and 2.45 g (0.0138 mol) of 2-methylamino-4,6-dichloro-pyrimidine were suspended in 22 ml of 1-methyl-2-pyrrolidone and stirred at 150° C. for 24 hours. The solvent was removed in a high vacuum and the residue was suspended in 250 ml of water. The mixture was extracted three times with 100 ml of ethyl acetate each time and the combined organic phases were washed with 200 ml of saturated NaHCO3. The combined aqueous phases were made acid with 3N HCl and the precipitate which thereby separated was filtered off under suction. It was chromatographed on silica gel with dichloromethane/methanol 99:1→98:2. The yellowish crystals obtained after the chromatography were suspended in 70 ml of 1N NaOH, the suspension was filtered and the clear filtrate was adjusted to pH 3.5 with 1N HCl. The precipitate which thereby separated was isolated and dried. There were obtained 1.9 g (46%) of N-(2-methylamino-6-chloro-pyrimidin-4-yl)-benzenesulfonamide as colorless crystals; m.p.: 186-187° C.

Workup

  1. customThe solvent was removed in a high vacuum
  2. extractionThe mixture was extracted three times with 100 ml of ethyl acetate each time
  3. washthe combined organic phases were washed with 200 ml of saturated NaHCO3
  4. customthe precipitate which thereby separated
  5. filtrationwas filtered off under suction
  6. customIt was chromatographed on silica gel with dichloromethane/methanol 99:1→98:2
  7. customThe yellowish crystals obtained after the chromatography
  8. filtrationthe suspension was filtered
  9. customThe precipitate which thereby separated
  10. customwas isolated
  11. customdried

Sources & evidence

ORD record
ord-2ca9d83fd5f3443fa8194cebddfd83ee
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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