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

HRID 570687Notes

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]

Participants

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

filtrationthe precipitated precipitate was collected by filtration
dissolutiondissolved in tetrahydrofuran (15 ml)
additionThe solution was diluted with ethyl acetate (30 ml)
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
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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