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p-Toluenesulfonic acid → Methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylate

HRID 450548
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HRID 450548 반응식
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([O:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]2[C:3]3[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[C:18]([O:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:17]=1
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참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 17965841Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylateHCID 584130794-Fluoro-2-(oxan-4-yloxy)aniline

생성물 1

HCID 46182082Methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylate수율 49%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylate (0.256 g, 1.12 mmol), 4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)aniline (0.236 g, 1.12 mmol) and para-toluene sulfonic acid (0.021 g, 0.01 mmol) were heated at reflux in anhydrous 1,4-dioxane (6 mL) for 4 hours. The solution was cooled, concentrated in vacuo and the crude product absorbed on to silica. The sample was purified by flash column chromatography (100% DCM→10% MeOH/DCM) to yield the title compound (0.220 g, 49%) after recrystallisation from MeOH.

후처리

  1. temperatureThe solution was cooled
  2. concentrationconcentrated in vacuo
  3. customthe crude product absorbed on to silica
  4. customThe sample was purified by flash column chromatography (100% DCM→10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-9138ab012659496ebd1435dcbcff1139
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486953B2

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