Pyridine → [4-(N,N-dimethylamino)quinazolin-6-yl]acrylamide

HRID 394727

Reaktionsgleichung

Reaktionsgleichung von HRID 394727
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].N1C=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:13][N:14]([CH3:23])[CH2:15][CH2:16][CH2:17][N:18]=[C:19]=[N:20]CC.CCOC(C)=O.C(Cl)Cl.CC([N:36](C)C)=O>C(Cl)Cl.CCCCCC.CO.C(Cl)Cl.CCOC(C)=O>[CH3:23][N:14]([C:15]1[C:16]2[C:17](=[CH:7][CH:8]=[C:9]([C:2](=[CH2:3])[C:1]([NH2:36])=[O:5])[CH:10]=2)[N:18]=[CH:19][N:20]=1)[CH3:13]

Komponenten

8

Edukt 5

HCID 1049PyridineHCID 6581Acrylic AcidHCID 31374DimethylacetamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226138Dichloromethane ethylacetate

Produkt 1

HCID 18176137[4-(N,N-dimethylamino)quinazolin-6-yl]acrylamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21226440Methylenechloride HexaneLösungsmittelHCID 21901258Dichloromethane ethyl acetate methanolLösungsmittel

Versuchsvorschrift

To a stirred solution containing the above 4-N,N-dimethylamino-6-aminoquinazoline (0.65 g, 3.45 mmol), acrylic acid (4 mol eq., 13.8 mmol, 0.95 mL), and pyridine (excess, 1.3 mL) in DMA (20 mL) under N2 was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (2 mol eq., 6.90 mmol, 1.32 g). The standard procedure above was followed to give after chromatography on silica gel eluting with EtOAc/CH2Cl2 (1:1) to MeOH/CH2Cl2/EtOAc (1:4:5), [4-(N,N-dimethylamino)quinazolin-6-yl]acrylamide (350 mg, 42%) as a cream powder, mp (CH2Cl2/hexane) 204-206° C.

Quellen und Nachweise

ORD-Eintrag
ord-fbf95f60aa1445efa08e9b6b71dab0f9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602863B1

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