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

HRID 378290

반응식

HRID 378290 반응식
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[K+].[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH-:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>CN1CCCC1=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:9][CH3:10])[N:5]=[C:6]([NH:22][S:19]([C:16]2[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH:7]=1

참가 물질

4

반응물 2

HCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 1317213244-Fluoro-benzenesulfonamide potassium salt

생성물 1

HCID 19353544N-(6-chloro-2-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide수율 56%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

0.46 g (0.0026 mol) of (4,6-dichloro-pyrimidin-2-yl)-methylamine and 1.1 g (0.0051 mol) of 4-fluoro-benzenesulfonamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone in 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 saturated with sodium chloride, evaporated briefly in a vacuum and made acid with 4N HCl, with a precipitate separating. The mixture was suctioned filtered, the extract and the solid were combined and chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent. The product was recrystallized from ethyl acetate/n-hexane. There was obtained 0.46 g (56%) of N-(6-chloro-2-methylamino-pyrimidin-4-yl)-4-fluoro-benzenesulfonamide as white crystals; m.p. 121-123C.

후처리

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. extractionextracted
  4. customevaporated briefly in a vacuum
  5. customwith a precipitate separating
  6. filtrationThe mixture was suctioned filtered
  7. extractionthe extract
  8. customchromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent
  9. customThe product was recrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-ba76fd18be1544219176b04f09dfd7fd
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030976

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