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

HRID 570689Notes

Reaction equation

HRID 570689 reaction equation
[CH2:1]([S:3][C:4]1[N:5]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][CH:18]=2)[C:6](=[O:16])[C:7]2[CH:13]=[CH:12][C:11]([O:14]C)=[N:10][C:8]=2[N:9]=1)[CH3:2].Cl.N1C=CC=CC=1.Cl>CN(C)C=O>[CH2:1]([S:3][C:4]1[N:5]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:27])([F:28])[F:26])=[CH:19][CH:18]=2)[C:6](=[O:16])[C:7]2[CH:13]=[CH:12][C:11](=[O:14])[NH:10][C:8]=2[N:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 680153302-(ethylsulfanyl)-7-methoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 866853532-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(ethylsulfanyl)-7-methoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (150 mg), pyridine hydrochloride (1156 mg) and N,N-dimethylformamide (1 ml) was stirred at 120° C. for 15 min. The reaction mixture was poured into 0.2M hydrochloric acid (10 ml), and the precipitated white solid was collected by filtration, and washed with water. The obtained solid was dissolved in tetrahydrofuran (5 ml), and the solution was diluted with ethyl acetate (70 ml), washed with saturated brine, 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 (137 mg) as a white solid.

Workup

  1. filtrationthe precipitated white solid was collected by filtration
  2. washwashed with water
  3. dissolutionThe obtained solid was dissolved in tetrahydrofuran (5 ml)
  4. additionthe solution was diluted with ethyl acetate (70 ml)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a7ace83272514e79970e41330a0e4039
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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