Acetic Acid → 4(1H)-Pyrimidinone, 2-(butylthio)-

HRID 1946981Notes

Reaction equation

HRID 1946981 reaction equation
[S:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][NH:3]1.[OH-].[Na+].[CH2:11](I)[CH2:12][CH2:13][CH3:14].C(O)(=O)C>O>[CH2:11]([S:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Procedure

2-Thioxo-2,3-dihydro-1H-pyrimidin-4-one (12.8 g) was added to a solution of NaOH (8.0 g) in water (70 mL). After complete dissolution of the solids butyl iodide (12.4 mL) was added to the solution and the resulting mixture was stirred at RT overnight. A second aliquot of butyl iodide (1.2 mL) was then added and the reaction mixture was stirred for 24 h. A third aliquot of butyl iodide (1.2 mL) was added and the resulting mixture was stirred for 6 days. Glacial acetic acid (5.5 mL) was added and the reaction mixture was stirred for 30 min, it was then stored at 4° C. overnight. The precipitate formed was collected by filtration and dried under reduced pressure to give 12.3 g of 2-butylsulfanyl-3H-pyrimidin-4-one.

Workup

  1. additionwas added to the solution
  2. stirringthe reaction mixture was stirred for 24 h
  3. stirringthe resulting mixture was stirred for 6 days
  4. stirringthe reaction mixture was stirred for 30 min
  5. waitit was then stored at 4° C. overnight
  6. customThe precipitate formed
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ebb20cb6aad14451816afaa1dea67da8
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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