Water → 8-(4'-Methylbiphenyl-4-ylmethylamino)adenosine

HRID 1713323노트

반응식

HRID 1713323 반응식
Br[C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]2[N:9]([C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:26])[C:24]=3[N:25]=2)[C@@H:10]2[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:11]2[OH:12])=[CH:4][CH:3]=1.[CH3:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(OCC)C.C(OC(=O)C)C.C(O)C>[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]3[N:9]([C:19]4[N:20]=[CH:21][N:22]=[C:23]([NH2:26])[C:24]=4[N:25]=3)[C@@H:10]3[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:11]3[OH:12])=[CH:4][CH:3]=2)=[CH:32][CH:31]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 674555318-(4-Bromobenzylamino)adenosine

생성물 1

HCID 116123488-(4'-Methylbiphenyl-4-ylmethylamino)adenosine수율 42.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 21584169Diethylether ethylacetate용매

실험 절차

To a mixture of 8-(4-bromobenzylamino)adenosine (0.050 g), 4-methylphenylboronic acid (0.017 g), sodium carbonate (0.024 g), water (0.4 mL) and ethanol (2.2 mL) was added tetrakis-(triphenylphosphine)palladium(0) (0.006 g), and the resulting mixture was stirred under reflux for 22 hours. The reaction mixture was cooled to room temperature. After addition of dichloromethane/methanol (5/1, 35 mL), the insoluble material was filtered out. The filtrate was concentrated under reduced pressure. The residue was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK C18MG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, eluent: water/methanol=70/30-10/90) to give the title compound (0.022 g).

후처리

  1. temperatureunder reflux for 22 hours
  2. filtrationthe insoluble material was filtered out
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK C18MG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, eluent: water/methanol=70/30-10/90)

출처 및 근거

ORD 기록
ord-fa3a32d9f049447d84029473abd5e88e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795236B2

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