Isopropanol → 4-Amino-1-benzylpyrimidin-2(1H)-one

HRID 538231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538231
CCCC[N+](CCCC)(CCCC)CCCC.[OH-].CC(O)C.[NH:23]1[CH:30]=[CH:29][C:27]([NH2:28])=[N:26][C:24]1=[O:25].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CO.CN(C=O)C>[NH2:28][C:27]1[CH:29]=[CH:30][N:23]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24](=[O:25])[N:26]=1

Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 7498Benzyl BromideHCID 2723671Tetrabutylammonium HydroxideHCID 178418229Cytosine

Produkt 1

HCID 3085814-Amino-1-benzylpyrimidin-2(1H)-oneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 0.1 M solution of tetra-N-butylammonium hydroxide in a mixture of MeOH and 2-propanol (90 mL, 9.0 mmol) was added dropwise to a stirred suspension of cytosine (1 g, 9.0 mmol) in DMF (70 mL). The solution became clear and benzyl bromide (2.14 mL, 18 mmol) was added dropwise. The reaction mixture was stirred at RT for 2 hours and then the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM with a gradient of 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 4-amino-1-benzyl-1H-pyrimidin-2-one (1 g, 57% yield) as a white solid.

Aufarbeitung

  1. customthe solvents were evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dacb25459be944318f45a77abc92edcb
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865725B2

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