Hydrochloric Acid → 2-(1-methylethoxy)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570702Notes

Reaction equation

HRID 570702 reaction equation
CS([C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1)=O.[CH3:28][CH:29]([OH:31])[CH3:30].[H-].[Na+].Cl>O1CCCC1>[CH3:28][CH:29]([O:31][C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1)[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 866853562-(methylsulfinyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 866853652-(1-methylethoxy)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Methylsulfinyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (100 mg) was suspended in tetrahydrofuran (4 ml), 2-propanol (77 μl) was added thereto, and then sodium hydride (25.0 mg) was added thereto under ice-cooling, and the mixture was stirred for 10 min, and then at room temperature for 15 min. To the reaction mixture was added 0.5M hydrochloric acid (3 ml), 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 white residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (35.4 mg) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. waitat room temperature for 15 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained white residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-afcefa0478ff4785a3a62b89115eb309
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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