Hydrochloric Acid → 5-Isopropylpyrimidin-2(1H)-one

HRID 2251496Notes

Reaction equation

HRID 2251496 reaction equation
C(O[CH:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[CH:6]=O)C.[NH2:11][C:12]([NH2:14])=[O:13].Cl.[OH-].[Na+]>C(O)C>[CH:8]([C:5]1[CH:6]=[N:11][C:12](=[O:13])[NH:14][CH:4]=1)([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 14798Sodium HydroxideHCID 772305003-Ethoxy-2-isopropylprop-2-enal

Product 1

HCID 123561535-Isopropylpyrimidin-2(1H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-ethoxy-2-isopropylprop-2-enal (ref. Menicagli, R. et al. Tetrahedron 1987, 43, 171–177) (250 mg, 1.76 mmol) and urea (250 mg, 4.16 mmol) in ethanol (2.5 ml) was treated with concentrated HCl (0.5 ml) and heated to reflux for 1 hour. Upon cooling, the reaction mixture was neutralized with 1N NaOH (0.6 ml) and extracted with chloroform. The organic layer was dried over MgSO4 and concentrated to provide 5-isopropylpyrimidin-2(1H)-one as an off-white solid (0.20 g; 82% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureUpon cooling
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8b2ddbdfac140caa5cebb30e69b1306
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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