1,3-Propanediamine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(3-aminopropyl)propanamide

HRID 1534951Notes

Reaction equation

HRID 1534951 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.[NH2:18][CH2:19][CH2:20][CH2:21][NH2:22].CCOCC.C(#N)C>CO>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:18][CH2:19][CH2:20][CH2:21][NH2:22])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

6

Reactant 4

HCID 4281,3-PropanediamineHCID 3283Diethyl Ether2×HCID 6342AcetonitrileHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1360404793-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(3-aminopropyl)propanamideYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to 1.85 g (25.0 mmol) of 1,3-diaminopropane in a 10 ml round bottom flask equipped with a magnetic stirring bar. The solution was stirred at room temperature for two hours. 10 ml ether was added and the solution was stirred for a few minutes. The ether solution was decanted, leaving an oil residue. 5 ml of acetonitrile and 4 ml of ether were added and the solution was stirred. Methanol was added dropwise until a precipitate had formed. The solution was filtered and washed with acetonitrile and ether, to yield 205 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-(3-aminopropyl)propanamide (AIT-0074). m.p. 172°-175° C. Yield: 73%

Workup

  1. customequipped with a magnetic stirring bar
  2. stirringthe solution was stirred for a few minutes
  3. customThe ether solution was decanted
  4. customleaving an oil residue
  5. stirringthe solution was stirred
  6. customhad formed
  7. filtrationThe solution was filtered
  8. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-89d89d64907a4d02beb3da5eda681fc2
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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