Ethyl 2-acetylhexanoate → 5-Butyl-6-methyl-2-thiouracil

HRID 1643206

Reaktionsgleichung

Reaktionsgleichung von HRID 1643206
[Na].[NH2:2][C:3]([NH2:5])=[S:4].CC[O-].[Na+].[CH2:10]([CH:14]([C:20]([CH3:22])=O)[C:15](OCC)=[O:16])[CH2:11][CH2:12][CH3:13]>CCO>[CH2:10]([C:14]1[C:15](=[O:16])[NH:2][C:3](=[S:4])[NH:5][C:20]=1[CH3:22])[CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 95466Ethyl 2-acetylhexanoateHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 27256805-Butyl-6-methyl-2-thiouracil

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium metal (1.85 g, 80.5 mmol) is dissolved in EtOH (50 mL). Next, thiourea (5.11 g, 67.1 mmol) is added to the NaOEt solution, followed by ethyl 2-n-butylacetoacetate (2.5 g, 13.4 mmol). The reaction mixture is stirred at reflux for 3 hours and then allowed to cool to room temperature overnight. The EtOH is removed in vacuo. The residue is then suspended in H2O (50 mL) and the resulting mixture carefully treated with concentrated HCl (−7.5 mL) just until pH 4 is reached. After stirring for 15 minutes, the suspension is filtered, and the solid thoroughly washed with H2O. Drying affords pure 5-butyl-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one as a slightly off-white solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.28 (br s, 1H), 12.05 (br s, 1H), 2.21 (m, 2H), 2.18 (s, 3H), 1.30-1.21 (m, 4H), 0.85 (t, J=6.9 Hz, 3H) ppm. MS; m/z 199 [M+1].

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customThe EtOH is removed in vacuo
  3. additionthe resulting mixture carefully treated with concentrated HCl (−7.5 mL) just until pH 4
  4. stirringAfter stirring for 15 minutes
  5. filtrationthe suspension is filtered
  6. washthe solid thoroughly washed with H2O
  7. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-943e2200a410422ab4b25cbdb2a37fd9
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119665B2

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