Triethylamine → 8-(4-Bromobenzylamino)adenosine

HRID 1713259Notes

Reaction equation

HRID 1713259 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].Cl.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.C(N(CC)CC)C>C(O)C>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][C:2]2[N:3]([C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=3[N:19]=2)[C@@H:4]2[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]2[OH:6])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 965448-BromoadenosineHCID 27240964-Bromobenzylamine hydrochloride

Product 1

HCID 674555318-(4-Bromobenzylamino)adenosineYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-bromoadenosine (0.100 g), 4-bromobenzylamine hydrochloride (0.193 g) and triethylamine (0.201 mL) in ethanol (2.9 mL) was stirred under reflux for 96 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.118 g).

Workup

  1. temperatureunder reflux for 96 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-639b01dafef94996920f61aa46db08fb
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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