Hydrochloric Acid → 7-methoxy-2-(2,2,2-trifluoroethoxy)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 570688Notes

Reaction equation

HRID 570688 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19]CC(F)(F)F)=[CH:15][CH:14]=3)[C:9](SCCC)=[N:8][C:7]=2[N:29]=1.[F:30][C:31]([F:35])([F:34])[CH2:32][OH:33].[H-].[Na+].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:32][C:31]([F:35])([F:34])[F:30])=[CH:15][CH:14]=3)[C:9]([O:33][CH2:32][C:31]([F:35])([F:34])[F:30])=[N:8][C:7]=2[N:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 68015336HCID 68015336, compound

Product 1

HCID 866853527-methoxy-2-(2,2,2-trifluoroethoxy)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Methoxy-2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (350 mg) and 2,2,2-trifluoroethanol (592 μl) were dissolved in tetrahydrofuran (3 ml), and sodium hydride (60% in oil, 165 mg) was added thereto at room temperature. The reaction mixture was heated under reflux for 3 days, and allowed to be cooled to room temperature, and poured into 0.5M hydrochloric acid (10 ml). The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained white solid was purified by silica gel column chromatography (ethyl acetate/hexane) and then (NH, ethyl acetate/hexane) to give the white title compound (63 mg).

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3 days
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained white solid was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02bc08701e3a45629d5d0519a2c77193
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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