Reaktionsgleichung
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]C(=O)C)=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of 0.95 g of 2-acetamido-4-hydroxy-6-[2-(4-acetoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 50 mL of water was added 1N aqueous sodium hydroxide until a homogenous solution was obtained. Acidification with acetic acid resulted in the formation of a yellow precipitate which was collected by filtration. The filter cake was washed sequentially with water, methanol, acetone and ether. The residual solid was recrystallized from DMF to give 0.65 g (77%) of the title compound, which can be alternatively named as 2-acetamido-6-(4-carboxystyryl)-5-deaza-4(3H)-pteridinone, as a microcrystalline yellow solid, mp>300° C.; NMR (TFA-d1) delta 2.5(s, 3H), 6.85, 7.32(AB q, 2H, J=12 Hz), 7.45, 8.18(AB q, 4H, J=9 Hz), 8.65(s, 1H), 9.02(s, 1H); IR (Nujol) 3300-2200(br), 1685, 1655, 1630, 1600, 1565 cm-1. MS: Calc'd. for C18H 14 N4O4 : 350. Found: m/e 350 (base), 308.
Aufarbeitung
- customwas obtained
- filtrationwas collected by filtration
- washThe filter cake was washed sequentially with water, methanol, acetone and ether
- customThe residual solid was recrystallized from DMF
Quellen und Nachweise
- ORD-Eintrag
- ord-818c93e1361b4efa852e0ef9f168f126
- Quelldatensatz
- uspto-grants-1991_06
- Patentnummer
- US05026851
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