Hydrazine hydrate (1:1) → 3-(6-Oxo-3,6-dihydro-9H-purin-9-yl)propanehydrazide

HRID 1534940Notes

Reaction equation

HRID 1534940 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]CC)=O)[CH:5]=[N:4][C:3]1=2.O.[NH2:19][NH2:20]>C(O)C>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:19][NH2:20])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1362413973-(6-Oxo-3,6-dihydro-9H-purin-9-yl)propanehydrazideYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.181 g (5.00 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was placed into a 25 ml flask equipped with a magnetic stirring bar. About 5 ml absolute ethanol was added and then 2.50 g (50.00 mmol) of hydrazine hydrate was added and the solution was stirred at room temperature in a closed flask. A large amount of precipitate formed after about 30 minutes and the solution was allowed to stand overnight. The solution was filtered by vacuum and the white solid was washed with ethanol and then with ether. Upon drying, 0.890 g of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid hydrazide (AIT-0056) as a white solid was obtained. Yield: 80%.

Workup

  1. customequipped with a magnetic stirring bar
  2. customA large amount of precipitate formed after about 30 minutes
  3. filtrationThe solution was filtered by vacuum
  4. washthe white solid was washed with ethanol
  5. customUpon drying

Sources & evidence

ORD record
ord-9d23d13dfa55404ab0a539089fa710a0
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

Loading…