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

HRID 1713323Notes

Reaction equation

HRID 1713323 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fa3a32d9f049447d84029473abd5e88e
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…