2-Bromobenzylamine → HCID 53683829, compound

HRID 1031863Notes

Reaction equation

HRID 1031863 reaction equation
[CH2:1]([C:3]1[C:4](=[O:28])[NH:5][C:6](=[O:27])[N:7]([CH:26]=1)[C@@H:8]1[O:25][C@H:12]([CH2:13]OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33]>CN(C=O)C.O.CO>[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][CH2:13][C@H:12]1[O:25][C@@H:8]([N:7]2[CH:26]=[C:3]([CH2:1][CH3:2])[C:4](=[O:28])[NH:5][C:6]2=[O:27])[CH2:9][C@@H:10]1[OH:11]

Participants

5

Reactant 2

HCID 3340722-BromobenzylamineHCID 5280128HCID 5280128, compound

Product 1

HCID 53683829HCID 53683829, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

2.5 g of 2'-deoxy-5-ethyl-5'-O-(p-toluenesulphonyl)-uridine were dissolved in 15 ml of DMF and added to 2-bromobenzylamine. The mixture was heated at 80° C. under nitrogen for 5 hours. The solvent was removed by evaporation and the residue was re-evaporated with toluene to give an oil. This was taken up in 20 ml of water/methanol (1:3) and stored in a refrigerator for 1.5 hours. A solid crystallized out and this was filtered off and washed with water/methanol (1:3) to give 0.99 g of 5'-(2-bromobenzylamino)-2',5'-dideoxy-5-ethyluridine, mp 144°-146° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was re-evaporated with toluene
  3. customto give an oil
  4. customA solid crystallized out
  5. filtrationthis was filtered off
  6. washwashed with water/methanol (1:3)

Sources & evidence

ORD record
ord-93ed4e68c1a84e349e8a7efed720aa20
Source dataset
uspto-grants-1990_09
Patent number
US04956346

Reaction notes

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