Hydrazine → HCID 178508936, compound

HRID 1382494Notes

Reaction equation

HRID 1382494 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7](Br)[N:8]2[CH2:11][O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[C:4]([OH:19])[N:3]=1.[NH2:20]N>O.[Ni]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([NH2:20])[N:8]2[CH2:11][O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[C:4]([OH:19])[N:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 178508917HCID 178508917, compound

Product 1

HCID 178508936HCID 178508936, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 2-[(2-amino-8-bromo-6-hydroxy-9H-purin-9-yl)methoxy]-1,3-propanediol (13.7 g; 41 mmole) and 97% hydrazine (6.07 ml) in water (300 ml) is heated to reflux for 48 hours. At the end of this time, the solution is cooled and filtered to give 9.15 g of crude solid. The crude product is suspended in water (120 ml) and Raney nickel (9 g) is added. The mixture is heated at reflux for 6 hours, filtered hot and cooled. The crystals are collected and dried to give 7.15 g of the product, mp>280° dec.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 48 hours
  3. temperatureAt the end of this time, the solution is cooled
  4. filtrationfiltered
  5. customto give 9.15 g of crude solid
  6. temperatureThe mixture is heated
  7. temperatureat reflux for 6 hours
  8. filtrationfiltered hot
  9. temperaturecooled
  10. customThe crystals are collected
  11. customdried

Sources & evidence

ORD record
ord-1e9dbcee265a40e58e1fbd0983b08569
Source dataset
uspto-grants-1989_02
Patent number
US04806642

Reaction notes

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