1,4-Dioxane → 4-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline

HRID 1416503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416503
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][CH:29]([OH:34])[CH:30]([OH:33])[CH2:31][OH:32])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.O1CCOCC1>CO.[Pd]>[OH:34][CH:29]([CH:30]([OH:33])[CH2:31][OH:32])[CH2:28][O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1

Komponenten

5

Edukt 2

HCID 312751,4-DioxaneHCID 675828332-[4-(Benzyloxycarbonyl)piperazin-1-yl]-4-[(2,3,4-trihydroxybutan-1-yl)oxy]quinazoline

Produkt 1

HCID 675821034-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazolineAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2,3,4-trihydroxybutan-1-yl)oxy]quinazoline (800 mg) in methanol (6 ml)--dioxane (6 ml) is added 10% palladium/carbon (160 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 17 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure. The residue is crystallized from acetone, and the resulting crystalline substance is recrystallized from ethanol-diethyl ether to give 4-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (316 mg) as crystals.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. customThe residue is crystallized from acetone
  4. customthe resulting crystalline substance is recrystallized from ethanol-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d3339fb909a7480da11b19d509def13c
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912247

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