2-(2-Aminoethyl)-1-methylpyrrolidine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]propanamide

HRID 1534935Notes

Reaction equation

HRID 1534935 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9].[O:10]=[C:11]1[NH:19][CH:18]=[N:17][C:16]2[N:15]([CH2:20][CH2:21][C:22](OCC)=[O:23])[CH:14]=[N:13][C:12]1=2>C(#N)C>[O:10]=[C:11]1[NH:19][CH:18]=[N:17][C:16]2[N:15]([CH2:20][CH2:21][C:22]([NH:1][CH2:2][CH2:3][CH:4]3[CH2:8][CH2:7][CH2:6][N:5]3[CH3:9])=[O:23])[CH:14]=[N:13][C:12]1=2

Participants

4

Reactant 2

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1361007143-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]propanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.565 g (4.41 mmol) of 2-(2-aminoethyl)-1-methylpyrrolidine was added to a 10 ml round bottom flask equipped with a magnetic stirring bar. The solution was heated and 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 and the solution was heated at 110°-120° C. for two hours. The orange solution was allowed to cool to room temperature and 8 ml acetonitrile was added and the solution was stirred for 20 minutes to wash the solid. The solution was filtered by Buchner vacuum filtration and the solid was washed with acetonitrile and then with ether. Upon drying 265 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]propanamide (AIT-0045) as a white solid was obtained.

Workup

  1. customequipped with a magnetic stirring bar
  2. temperatureThe solution was heated
  3. temperaturethe solution was heated at 110°-120° C. for two hours
  4. washto wash the solid
  5. filtrationThe solution was filtered by Buchner vacuum filtration
  6. washthe solid was washed with acetonitrile
  7. dry with materialUpon drying 265 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]propanamide (AIT-0045) as a white solid
  8. customwas obtained

Sources & evidence

ORD record
ord-1ebaceb48a874ce1ae7c871941fc3440
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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