Diisopropylethylamine → 8-(Biphenyl-4-ylmethylamino)-2'-deoxyadenosine

HRID 1713331Notes

Reaction equation

HRID 1713331 reaction equation
Br[C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1.[C:20]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>C(O)CC>[C:20]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=[CH:22][C:23]([CH2:26][NH:27][C:2]2[N:3]([C:12]3[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=3[N:18]=2)[C@@H:4]2[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 965478-Bromo-2'-deoxyadenosineHCID 3449894-Phenylbenzylamine

Product 1

HCID 594604968-(Biphenyl-4-ylmethylamino)-2'-deoxyadenosineYield 54.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 8-bromo-2′-deoxyadenosine (0.07 g), biphenyl-4-ylmethylamine (0.12 g) and N,N-diisopropyl-ethylamine (0.15 mL) in 1-propanol (2.1 mL) was stirred under reflux for 24 hours. The reaction mixture was cooled to room temperature and 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 (0.05 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-8252cdeedc4646ae9d662caac0ad7e92
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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