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Hydrochloric Acid → 2-ethoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570692
Notes
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Reaction equation

HRID 570692 reaction equation
CS[C:3]1[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:17][CH:16]=2)[C:5](=[O:14])[C:6]2[CH:12]=[CH:11][C:10](=[O:13])[NH:9][C:7]=2[N:8]=1.[O-:27][CH2:28][CH3:29].[Na+].Cl>C(O)C>[CH2:28]([O:27][C:3]1[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:17][CH:16]=2)[C:5](=[O:14])[C:6]2[CH:12]=[CH:11][C:10](=[O:13])[NH:9][C:7]=2[N:8]=1)[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 866853542-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 866853552-ethoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

2-(Methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (300 mg) was suspended in ethanol (9 ml), sodium ethoxide (20% ethanol solution, 1.33 g) was added thereto at room temperature, and the mixture was heated under reflux for 3 hr, and allowed to be cooled. The reaction mixture was poured into 0.5M hydrochloric acid (9 ml) under ice-cooling, and the brown precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran (100 ml). The solution was diluted with ethyl acetate (150 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained brown residue was purified by silica gel column chromatography (ethyl acetate/hexane) and then silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (251 mg) as a white solid.

Workup

  1. temperatureunder reflux for 3 hr
  2. temperatureto be cooled
  3. temperaturecooling
  4. filtrationthe brown precipitate was collected by filtration
  5. washwashed with water
  6. dissolutiondissolved in tetrahydrofuran (100 ml)
  7. additionThe solution was diluted with ethyl acetate (150 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained brown residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-137178e3b9de4ea29e4fb31650d0d959
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023858B2

Reaction notes

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