N-(3-Aminopropyl)morpholine → 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(4-morpholinyl)propyl]propanamide
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[O:11]=[C:12]1[NH:20][CH:19]=[N:18][C:17]2[N:16]([CH2:21][CH2:22][C:23](OCC)=[O:24])[CH:15]=[N:14][C:13]1=2>C(#N)C>[O:11]=[C:12]1[NH:20][CH:19]=[N:18][C:17]2[N:16]([CH2:21][CH2:22][C:23]([NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:24])[CH:15]=[N:14][C:13]1=2Participants
Procedure
475 mg (3.29 mmol) of 4-(3-aminopropyl)morpholine was added to a 10 ml round bottom flask equipped with a magnetic stirring bar. The flask was heated to 100°-120° C. and 250 mg (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 flask. Heating was continued for two hours. The solution was allowed to cool to room temperature and was then treated with 8 ml acetonitrile with stirring. A white precipitate formed and the solution was filtered after 20 minutes of stirring in acetonitrile. The filtrate was washed with acetonitrile and then with ether. This yielded 130 mg of a white solid. The mother liquor was allowed to stand overnight in a fume hood and was filtered the next day to yield another 100 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(4-morpholinyl)propyl]propanamide (AIT-0043). Yield: 65%. m.p. 145°-148° C.
Workup
- customequipped with a magnetic stirring bar
- temperatureThe flask was heated to 100°-120° C.
- temperatureHeating
- customA white precipitate formed
- filtrationthe solution was filtered after 20 minutes
- stirringof stirring in acetonitrile
- washThe filtrate was washed with acetonitrile
- waitto stand overnight in a fume hood
- filtrationwas filtered the next day
Sources & evidence
- ORD record
- ord-54de925e9a1147979e808cba8715b99a
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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