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

HRID 1713323ノート

反応式

HRID 1713323 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 116123488-(4'-Methylbiphenyl-4-ylmethylamino)adenosine収率 42.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 21584169Diethylether ethylacetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fa3a32d9f049447d84029473abd5e88e
出典データセット
uspto-grants-2010_09
特許番号
US07795236B2

反応ノート

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