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

HRID 570719Notes

Reaction equation

HRID 570719 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[O:18])[N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:21][CH:20]=4)[C:15](=[S:31])[NH:14][C:13]=3[N:32]=2)=[CH:5][CH:4]=1.I[CH2:36][CH3:37].[OH-].[Na+].Cl>O.CN(C)C=O>[CH2:36]([S:31][C:15]1[N:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([F:29])([F:28])[F:30])=[CH:21][CH:20]=2)[C:17](=[O:18])[C:12]2[CH:11]=[CH:10][C:9]([NH:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=3)=[N:32][C:13]=2[N:14]=1)[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 866853787-[(4-methoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one

Product 1

HCID 866853792-(ethylsulfanyl)-7-[(4-methoxybenzyl)amino]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

7-[(4-Methoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (108 mg), iodoethane (53 μl) and 1M aqueous sodium hydroxide solution (220 μl) were added to N,N-dimethylformamide (2 ml), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture were added 1M hydrochloric acid and water, and the mixture was 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 (NH, ethyl acetate/hexane) to give the white title compound (63 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0da56619eb8c4f268b9a4f13ab3d89e4
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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