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

HRID 883553

Reaktionsgleichung

Reaktionsgleichung von HRID 883553
[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-9286a1562b1f46d699441107d5ceab03
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236951B2

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