Dimethylformamide → 7-methoxy-2-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 570685Notes

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](=[S:25])[NH:8][C:7]=2[N:26]=1.[C:27](=O)([O-])O.[Na+].IC.CN(C)C=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=3)[C:9]([S:25][CH3:27])=[N:8][C:7]=2[N:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-methoxy-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (1.2 g), 1M aqueous sodium hydrogen carbonate solution (3.1 ml), iodomethane (0.98 ml) and N,N-dimethylformamide (10 ml) was stirred at 60° C. for 1 hr. The reaction mixture was allowed to be cooled, diluted with ethyl acetate (100 ml), washed with water and 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 (NH, ethyl acetate/hexane) to give the title compound (1.24 g).

Workup

temperatureto be cooled
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e653fe4fa0e041cca53d7783ac01b2d8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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