Trifluoroacetic acid → 7-amino-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one
Reaction equation
[CH2:1]([S:3][C:4]1[N:5]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:27][CH:26]=2)[C:6](=[O:24])[C:7]2[CH:13]=[CH:12][C:11]([NH:14]CC3C=CC(OC)=CC=3)=[N:10][C:8]=2[N:9]=1)[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[NH2:14][C:11]1[CH:12]=[CH:13][C:7]2[C:6](=[O:24])[N:5]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:29][CH:30]=3)[C:4]([S:3][CH2:1][CH3:2])=[N:9][C:8]=2[N:10]=1Participants
5
Reactant 4
Product 1
Procedure
2-(Ethylsulfanyl)-7-[(4-methoxybenzyl)amino]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (63 mg) and anisole (26 μl) were added to trifluoroacetic acid (1 ml), and the mixture was heated under reflux for 1 hr and 30 min. The reaction mixture was basified with saturated aqueous sodium hydrogen carbonate solution, and 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 residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (29 mg) as a white solid.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 1 hr and 30 min
- extractionextracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ab51c3f660bc46a7a2b042083f836508
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023858B2
Reaction notes
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