Cyclopentylamine → N-cyclopentyl-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2-amine

HRID 1836976

반응식

HRID 1836976 반응식
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)(=O)=O.[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1>CC#N>[CH:25]1([NH:30][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

4

반응물 2

HCID 2906CyclopentylamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

생성물 1

HCID 9821491N-cyclopentyl-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2-amine수율 53%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.50 g, 1.31 mmol) in MeCN (10 ml) was added cyclopentylamine (0.34 g) and the resultant solution heated under reflux for 18 h. The cooled reaction mixture was concentrated in vacuo and the residue partitioned between 2N HCl and ethyl acetate. The organic phase was separated, washed with 2N HCl then water and concentrated in vacuo to a yellow oil. This oil was purified by SPE chromatography with cyclohexane:ethyl acetate (3:1) as eluant. Concentration in vacuo of the combined fractions containing pure product gave crystals which were isolated by filtration to give the title compound as a white crystalline solid (0.21 g, 53%).

후처리

  1. temperatureunder reflux for 18 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue partitioned between 2N HCl and ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with 2N HCl
  7. concentrationwater and concentrated in vacuo to a yellow oil
  8. customThis oil was purified by SPE chromatography with cyclohexane:ethyl acetate (3:1) as eluant
  9. concentrationConcentration in vacuo of the combined fractions
  10. additioncontaining pure product
  11. customgave crystals which
  12. customwere isolated by filtration

출처 및 근거

ORD 기록
ord-11f08ec5f5df49d4b11758e1014454fe
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780869B1

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