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 570718노트

반응식

HRID 570718 반응식
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

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1cd05c3696ef43ce9d405be335535067
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023858B2

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