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

HRID 1534946Notes

Reaction equation

[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[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:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[O:22])[CH:13]=[N:12][C:11]1=2

Participants

Conditions

Temperature: 110 °C

Procedure

0.500 g (4.30 mmol) of N,N-diethylethylenediamine was placed into a 10 ml round bottom flask equipped with a magnetic stirring bar. The amine was heated to 110° C. 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 to the stirring solution. The solution was heated for one hour at 110° C. and was allowed to cool to room temperature. 10 ml of acetonitrile was added and the solution was stirred for 15 minutes. The white precipitate was obtained by filtration and was washed with acetonitrile and then with ether. Upon drying, 195 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(diethylamino)ethyl]propanamide (AIT-0064) as a white solid was obtained. Yield: 60%.

Workup

customequipped with a magnetic stirring bar
temperatureto cool to room temperature
customThe white precipitate was obtained by filtration
washwas washed with acetonitrile
customUpon drying

Sources & evidence

ORD record: ord-bb05ad6fcaf845688580450a53d1a98c
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091432

Reaction notes

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