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

HRID 1713324Notes

Reaction equation

HRID 1713324 reaction equation
Br[C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6].[CH2:21]([O:28][C:29]1[CH:30]=[C:31]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[CH:37][CH:36]=2)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C>C(O)CC>[CH2:21]([O:28][C:29]1[CH:30]=[C:31]([C:35]2[CH:36]=[CH:37][C:38]([CH2:41][NH:42][C:2]3[N:3]([C:13]4[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=4[N:19]=3)[C@@H:4]3[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]3[OH:6])=[CH:39][CH:40]=2)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 965448-BromoadenosineHCID 230050193'-Benzyloxybiphenyl-4-ylmethylamine

Product 1

HCID 594603638-(3'-Benzyloxybiphenyl-4-ylmethylamino)adenosineYield 57.6%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of a 8-bromoadenosine (0.130 g), 3′-benzyloxy-biphenyl-4-ylmethylamine (0.326 g) and N,N-diisopropyl-ethylamine (0.262 mL) in 1-propanol (3.8 mL) was stirred under reflux for 24 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue was purified by column chromatography on amino-propylated silica gel (eluent: dichloromethane/methanol=12/1) to give the title compound (0.120 g).

Workup

  1. temperatureunder reflux for 24 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on amino-propylated silica gel (eluent: dichloromethane/methanol=12/1)

Sources & evidence

ORD record
ord-2201998c364943a9adf25318596899d0
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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