Ethyl Acetate → 2-(5-aminopyridin-2-yl)-6-chloro-5-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-(2,2,2-trifluoroethyl)pyrimidin-4-amine

HRID 2112614노트

반응식

HRID 2112614 반응식
[H-].[Na+].[CH3:3][N:4]([CH:6](O)[CH2:7][CH3:8])[CH3:5].[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:22]=[C:21]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:20]([C:29]3[C:34]([F:35])=[CH:33][C:32](F)=[CH:31][C:30]=3[F:37])=[C:19]([Cl:38])[N:18]=2)=[N:15][CH:16]=1.C(OCC)(=[O:41])C>CSC>[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:22]=[C:21]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:20]([C:29]3[C:34]([F:35])=[CH:33][C:32]([O:41][CH2:8][CH2:7][CH2:6][N:4]([CH3:5])[CH3:3])=[CH:31][C:30]=3[F:37])=[C:19]([Cl:38])[N:18]=2)=[N:15][CH:16]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 116739Propanol, (dimethylamino)-HCID 865974612-(5-aminopyridin-2-yl)-6-chloro-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine

생성물 1

HCID 865974622-(5-aminopyridin-2-yl)-6-chloro-5-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-(2,2,2-trifluoroethyl)pyrimidin-4-amine

시약·촉매·용매 1

HCID 1068Dimethyl Sulfide용매

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온도
60 °C

실험 절차

To a mixture of sodium hydride (33.6 mg, 0.84 mmol) in 2 mL of dimethylsulfide is added N,N-Dimethylaminopropan-1-ol (99 μL, 0.84 mmol) slowly. After 30 minutes, 2-(5-aminopyridin-2-yl)-6-chloro-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine (100 mg, from Step A) is added and the resulting reaction mixture is heated at 60° C. for 4 h. The reaction mixture is cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with water and then with saturated sodium chloride solution, dried over magnesium sulfate, filtered, concentrated and dried under reduced pressure to yield 2-(5-aminopyridin-2-yl)-6-chloro-5-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-(2,2,2-trifluoroethyl)pyrimidin-4-amine as a yellow semi-solid (60 mg). MS: m/z 517.3 (M+H). This product was used in the next step without further purification.

후처리

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture is cooled to room temperature
  3. washThe organic layer is washed with water
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-654a56932d5b430e9c85b817ccac46de
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524849B2

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