8-(3'-Benzyloxybiphenyl-4-ylmethylamino)adenosine → 8-(3'-Hydroxybiphenyl-4-ylmethylamino)adenosine

HRID 1713327Notes

Reaction equation

HRID 1713327 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]3[N:24]([C:34]4[N:35]=[CH:36][N:37]=[C:38]([NH2:41])[C:39]=4[N:40]=3)[C@@H:25]3[O:33][C@H:30]([CH2:31][OH:32])[C@@H:28]([OH:29])[C@H:26]3[OH:27])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]3[N:24]([C:34]4[N:35]=[CH:36][N:37]=[C:38]([NH2:41])[C:39]=4[N:40]=3)[C@@H:25]3[O:33][C@H:30]([CH2:31][OH:32])[C@@H:28]([OH:29])[C@H:26]3[OH:27])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 594603638-(3'-Benzyloxybiphenyl-4-ylmethylamino)adenosine

Product 1

HCID 594604808-(3'-Hydroxybiphenyl-4-ylmethylamino)adenosineYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-(3′-benzyloxybiphenyl-4-ylmethyl-amino)adenosine (0.103 g) and 10% palladium on carbon (55.4 wt % H2O, 0.047 g) in methanol (7.4 mL) was stirred at room temperature for 17.5 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1 to 6/1) to give the title compound (0.081 g).

Workup

  1. filtrationThe insoluble material was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1 to 6/1)

Sources & evidence

ORD record
ord-23317bac68204da2add70d1d0e5779c5
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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