Water → 2-(ethylsulfanyl)-7-(hydroxymethyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 570723Notes

Reaction equation

HRID 570723 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:22][CH:21]=3)[C:16](=[S:32])[NH:15][C:14]=2[N:33]=1)(C(C)(C)C)(C)C.[F-].[CH2:35]([N+](CCCC)(CCCC)CCCC)[CH2:36]CC.O>O1CCCC1>[CH2:35]([S:32][C:16]1[N:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])=[CH:24][CH:25]=2)[C:18](=[O:19])[C:13]2[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[N:33][C:14]=2[N:15]=1)[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 866853837-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one

Product 1

HCID 866853842-(ethylsulfanyl)-7-(hydroxymethyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (498 mg) was suspended in tetrahydrofuran (15 ml), a tetrahydrofuran solution (1M, 3 ml) of tetrabutylammonium fluoride was added thereto, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (15 ml), iodoethane (0.24 ml) and 1M aqueous sodium hydrogen carbonate solution (1 ml) were added thereto, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added 1M hydrochloric acid and water, and the precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate/hexane to give the title compound (373 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (15 ml)
  6. additioniodoethane (0.24 ml) and 1M aqueous sodium hydrogen carbonate solution (1 ml) were added
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. additionTo the reaction mixture were added 1M hydrochloric acid and water
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water
  11. dissolutiondissolved in tetrahydrofuran
  12. dry with materialThe solution was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was recrystallized from a mixed solvent of ethyl acetate/hexane

Sources & evidence

ORD record
ord-6a18250586764694928e93b0890d1a65
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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