Potassium Carbonate → 7-[(4-methoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one

HRID 570718Notes

Reaction equation

HRID 570718 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:13]=3)[C:8](=[S:24])[NH:7][C:6]=2[N:25]=1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>[Cu]I.O.CN(C)C=O>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[O:11])[N:9]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:13]=4)[C:8](=[S:24])[NH:7][C:6]=3[N:25]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 754524-MethoxybenzylamineHCID 866853777-chloro-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 866853787-[(4-methoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 7-chloro-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (200 mg), 4-methoxybenzylamine (181 μl), copper(I) iodide (57 mg), potassium carbonate (166 mg) and N,N-dimethylformamide (3 ml) was stirred at 130° C. for 2 hr. To the reaction mixture were added saturated aqueous ammonium chloride solution and water, and the precipitate was collected by filtration, and dissolved in tetrahydrofuran. The solution was filtered through celite, and concentrated under reduced pressure. The residue was dissolved in a mixed solvent of ethyl acetate/tetrahydrofuran, and the solution was washed with aqueous ammonia solution 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 white title compound (108 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutiondissolved in tetrahydrofuran
  3. filtrationThe solution was filtered through celite
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in a mixed solvent of ethyl acetate/tetrahydrofuran
  6. washthe solution was washed with aqueous ammonia solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1cd05c3696ef43ce9d405be335535067
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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