Dimethylformamide → 7,8-Dimethoxy-4-amino-2-[4-(2-furoyl)piperazin-1-yl]quinazoline

HRID 354825

Reaktionsgleichung

Reaktionsgleichung von HRID 354825
[CH3:1][O:2][C:3]1[C:4]([NH2:13])=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]#[N:7].C[N:15](C)C=O.Cl.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33](=N)OCC)[CH2:29][CH2:28]1)=[O:26].[H-].[Na+]>O>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([C:6]([NH2:15])=[N:7][C:33]([N:30]3[CH2:31][CH2:32][N:27]([C:25]([C:21]4[O:20][CH:24]=[CH:23][CH:22]=4)=[O:26])[CH2:28][CH2:29]3)=[N:13]2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 187789902-Amino-3,4-dimethoxybenzonitrileHCID 20506452Ethyl 4-(2-furoyl)piperazin-1-ylformimidate hydrochloride

Produkt 1

HCID 129200147,8-Dimethoxy-4-amino-2-[4-(2-furoyl)piperazin-1-yl]quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.78 g. (0.01 mole) 3,4-dimethoxy-2-aminobenzonitrile in 30 ml. of N,N-dimethylformamide is added 2.88 g. (0.01 mole) ethyl 4-(2-furoyl)piperazin-1-ylformimidate hydrochloride followed by 855 mg. (0.02 mole) of a 56.1% dispersion of sodium hydride in mineral oil. The reaction mixture is stirred at ambient temperature for 30 minutes, and then it is heated to ca. 100° C. and maintained at that temperature for 12 hours. The reaction mixture is cooled to ambient temperature, diluted with an excess of water, and then extracted with chloroform. The chloroform extract is washed several times with water, dried using anhydrous magnesium sulfate, and then evaporated to dryness in vacuo. This affords crude 7,8-dimethoxy-4-amino-2-[4-(2-furoyl)piperazin-1-yl]quinazoline, which is purified further by recrystallization from aqueous ethanol.

Aufarbeitung

  1. temperatureit is heated to ca. 100° C.
  2. temperaturemaintained at that temperature for 12 hours
  3. temperatureThe reaction mixture is cooled to ambient temperature
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed several times with water
  7. customdried
  8. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd3efd42fee9452f99c9a7ee85a8f6e5
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377581

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