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

HRID 1534931Notes

Reaction equation

HRID 1534931 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][C:21]1[N:22]([CH3:26])[CH:23]=[CH:24][CH:25]=1>CCOCC.CC(C)=O>[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][C:21]3[N:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

4

Reactant 2

HCID 5650581-methyl-1H-pyrrole-2-ethylamineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1361162993-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrol-2-yl)ethyl] propanamideYield 80%

Reagents, catalysts & solvents 1

HCID 21584533Acetone diethyletherSolvent

Procedure

250 mg (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (Alt-0027) and 400 mg (3.22 mmol) of 2-(2-aminoethyl)-1-methyl-pyrrole were heated together in a 10 ml round bottom flask with stirring (no solvent) at 110°-120° C. for 3.5 hours. The dark viscous residue was treated with a 1:1 mixture of ether/acetone and stirred vigorously for 30 minutes. The precipitate was collected by filtration and was washed with ether and acetone and dried in vacuo to yield 265 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(1-methylpyrrol-2-yl)ethyl] propanamide (AIT-0035) as an off-white solid. Yield: 80%

Workup

  1. stirringstirred vigorously for 30 minutes
  2. filtrationThe precipitate was collected by filtration
  3. washwas washed with ether and acetone
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cd3bf61195cd401d95d1e9b06e3042af
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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