Ethanol → 6-Hydroxy-2-isobutylpyrimidin-4(3H)-one

HRID 1971036Notes

Reaction equation

HRID 1971036 reaction equation
[Na].C(O)C.Cl.[CH3:6][CH:7]([CH3:12])[CH2:8][C:9](=[NH:11])[NH2:10].[C:13](OCC)(=[O:20])[CH2:14][C:15](OCC)=[O:16]>O.C(O)(=O)C>[CH2:8]([C:9]1[N:10]=[C:15]([OH:16])[CH:14]=[C:13]([OH:20])[N:11]=1)[CH:7]([CH3:12])[CH3:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 5360545Sodium2×HCID 189679323-Methylbutanimidamide hydrochloride

Product 1

HCID 1784418736-Hydroxy-2-isobutylpyrimidin-4(3H)-oneYield 81.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium (0.75 g, 32.94 mmol) and ethanol (20 mL) were introduced in a flask. Once all the sodium had dissolved, 3-methylbutanimidamide hydrochloride (1.5 g, 10.98 mmol) and diethyl malonate (1.67 mL, 10.98 mmol) were added. It was stirred for 1 hour at room temperature and for 5 hours under reflux. The reaction crude was cooled at room temperature and concentrated to dryness. The solid obtained was dissolved in water and the pH was adjusted to 5 with acetic acid. The precipitate formed was filtered providing 1.5 g of the title compound (yield: 81%).

Workup

  1. temperatureunder reflux
  2. customThe reaction crude
  3. temperaturewas cooled at room temperature
  4. concentrationconcentrated to dryness
  5. customThe solid obtained
  6. customThe precipitate formed
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-99b64c948ac6444ca05f627cd25b3fcf
Source dataset
uspto-grants-2013_04
Patent number
US08431580B2

Reaction notes

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