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 2112614Notes

Reaction equation

HRID 2112614 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-654a56932d5b430e9c85b817ccac46de
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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