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 570718ノート

反応式

HRID 570718 の反応式
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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1cd05c3696ef43ce9d405be335535067
出典データセット
uspto-grants-2015_05
特許番号
US09023858B2

反応ノート

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