Acetic Anhydride → 6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one

HRID 31065

Reaktionsgleichung

Reaktionsgleichung von HRID 31065
[C:1](CC(O)=O)#[N:2].C(O[C:11](=[O:13])[CH3:12])(=O)C.[CH2:14]([NH:18][C:19]([NH:21][CH3:22])=[S:20])[CH:15]([CH3:17])[CH3:16].[OH-].[Na+]>C(O)C>[NH2:2][C:1]1[N:18]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:19](=[S:20])[N:21]([CH3:22])[C:11](=[O:13])[CH:12]=1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 14798Sodium HydroxideHCID 155682431-Isobutyl-3-methylthiourea

Produkt 1

HCID 866010566-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-oneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of cyanoacetic acid (1.52 g, 17.8 mmol) in acetic anhydride (2.45 mL, 25.9 mmol) was added to 1-isobutyl-3-methylthiourea (2.37 g, 16.2 mmol). The reaction mixture was heated to 60° C. for 1.5 h. The solvent was evaporated and the resulting red oil was redissolved in ethanol (5 mL) and 5M sodium hydroxide (1.6 mL, 8.1 mmol) was added. The reaction mixture was refluxed for 2 h. The solvent was co-evaporated with ethanol and the resulting pale brown solid was purified by flash chromatography (ethyl acetate) to yield 6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one (1.0 g, 29%) as a yellow solid.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe resulting red oil was redissolved in ethanol (5 mL)
  3. temperatureThe reaction mixture was refluxed for 2 h
  4. customthe resulting pale brown solid was purified by flash chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1ed6a4e0efb34e3d84ef3149d73d0e7f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425560B2

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