Acetonitrile → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]propanamide

HRID 1534928Notes

Reaction equation

HRID 1534928 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.C(#N)C.[NH2:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH2:28][CH3:29]>CCOCC>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:21][CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH2:28][CH3:29])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1361600303-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]propanamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-(1.6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (250 mg. 1.06 mol) (AIT-0027) was placed into a 10 ml round bottom flask equipped with a magnetic stirring bar, reflux condenser and CaCl2 drying tube. Then 3 ml acetonitrile and 280 mg (2.18 mmol) 2-(aminomethyl)-1-ethyl-pyrrolidine were added and the solution was heated to reflux. Not all of the ester dissolved at reflux, but as the reaction proceeded, the solution became homogeneous. Reflux was continued for 17 hours, at which time the solvent had completely evaporated. The residue was treated with acetonitrile and allowed to cool. A white precipitate had formed. Ether was added and the solution was stirred to wash the precipitate. The solution was filtered by Buchner vacuum filtration and the precipitate was washed with ether. Upon drying, 300 mg (0.94 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]propanamide (AIT-0029) was obtained as an off-white solid.

Workup

  1. customequipped with a magnetic stirring bar
  2. temperaturereflux condenser and CaCl2 drying tube
  3. temperaturethe solution was heated to reflux
  4. temperatureat reflux
  5. temperatureReflux
  6. customthe solvent had completely evaporated
  7. additionThe residue was treated with acetonitrile
  8. temperatureto cool
  9. customA white precipitate had formed
  10. washto wash the precipitate
  11. filtrationThe solution was filtered by Buchner vacuum filtration
  12. washthe precipitate was washed with ether
  13. customUpon drying

Sources & evidence

ORD record
ord-9459ddfdbaf24f879aa60250657a8e07
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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