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

HRID 1534948Notes

Reaction equation

HRID 1534948 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[O:9]=[C:10]1[NH:18][CH:17]=[N:16][C:15]2[N:14]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:13]=[N:12][C:11]1=2>C(#N)C>[O:9]=[C:10]1[NH:18][CH:17]=[N:16][C:15]2[N:14]([CH2:19][CH2:20][C:21]([NH:1][CH2:2][CH2:3][N:4]3[CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:22])[CH:13]=[N:12][C:11]1=2

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1360453183-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-pyrrolidinyl)ethyl]propanamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.500 g. (4.38 mmol) of 1-(2-aminoethyl)-pyrrolidine was heated 100°-110° C. with 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) in a 10 ml round bottom flask with stirring for one hour. Then, 10 ml of acetonitrile was added and the solution was stirred for 15 minutes. The resulting precipitate was collected by vacuum filtration. The solid was washed with acetonitrile and then with ether to yield 275 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-pyrrolidinyl)ethyl]propanamide (AIT-0068) as a white solid. Yield: 85%.

Workup

  1. stirringthe solution was stirred for 15 minutes
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washThe solid was washed with acetonitrile

Sources & evidence

ORD record
ord-52f730707e2e4f3384e5ffa8cb385bee
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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