2-Fluoroadenosine → 2-Hydrazinoadenosine

HRID 535290Notes

Reaction equation

HRID 535290 reaction equation
F[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].O.[NH2:22][NH2:23]>C(O)C>[NH:22]([C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])[NH2:23]

Participants

4

Reactant 2

HCID 89752-FluoroadenosineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 103572622-HydrazinoadenosineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-fluoroadenosine (4 g, 14 mmol) was dissolved in 100 mL ethanol in a 300 mL three-necked flask. Hydrazine hydrate (4.1 mL, 6 equivalents, 84 mmol) was added and the mixture was heated to reflux for 1 hour. The reaction mixture was allowed to cool to room temperature and stirred overnight (16 hours). The resulting white precipitate was isolated by filtration and dried in oven at 40° C. overnight to afford 2-hydrazinoadenosine (yield: 94%, 3.5 g, 96% purity).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe resulting white precipitate was isolated by filtration
  4. customdried in oven at 40° C. overnight

Sources & evidence

ORD record
ord-c6f777c2b7b3416ca41bff7522c73616
Source dataset
uspto-grants-2014_10
Patent number
US08859522B2

Reaction notes

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