Water → 2-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570705Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3,5,6-tetrahydropyrido[2,3-d]pyrimidine-4,7(1H,8H)-dione (2.05 g) in acetonitrile (40 mL) were added 1M aqueous sodium hydrogen carbonate solution (5.52 mL) and iodomethane (1.73 mL), and the mixture was stirred at 50° C. for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.1 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2b0db0295c144813ac67a77166346962
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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