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 2112614ノート

反応式

HRID 2112614 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 1068Dimethyl Sulfide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-654a56932d5b430e9c85b817ccac46de
出典データセット
uspto-grants-2009_04
特許番号
US07524849B2

反応ノート

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