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

HRID 570687
Notes
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Reaction equation

HRID 570687 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][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][CH:14]=3)[C:9](SCCC)=[N:8][C:7]=2[N:29]=1.[O-:30][CH2:31][CH3:32].[Na+].Cl>C(O)C>[CH2:31]([O:30][C:9]1[N:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([F:22])([F:23])[F:24])=[CH:17][CH:18]=2)[C:11](=[O:12])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:29][C:7]=2[N:8]=1)[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 68015336HCID 68015336, compound

Product 1

HCID 680153322-ethoxy-7-methoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-oneYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

7-Methoxy-2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (200 mg) was dissolved in ethanol (15 ml), sodium ethoxide (20% ethanol solution, 850 mg) was added thereto, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was poured into 0.2M hydrochloric acid (15 ml), and the precipitated precipitate was collected by filtration, and dissolved in tetrahydrofuran (15 ml). The solution was diluted with ethyl acetate (30 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (95 mg).

Workup

  1. filtrationthe precipitated precipitate was collected by filtration
  2. dissolutiondissolved in tetrahydrofuran (15 ml)
  3. additionThe solution was diluted with ethyl acetate (30 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1472719d772441418b48656cd047fd1f
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes