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

HRID 1643206

Reaction equation

HRID 1643206 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-943e2200a410422ab4b25cbdb2a37fd9
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Linked notes

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