1-(3,3-Diethoxypropyl)tetrahydropyrimidin-2-one → 3-(2-Oxo-tetrahydropyrimidin-1-yl)propionaldehyde

HRID 10189Notes

Reaction equation

HRID 10189 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:13])C>O1CCCC1>[O:13]=[C:8]1[NH:9][CH2:10][CH2:11][CH2:12][N:7]1[CH2:6][CH2:5][CH:4]=[O:3]

Participants

3

Reactant 1

HCID 692247861-(3,3-Diethoxypropyl)tetrahydropyrimidin-2-one

Product 1

HCID 840326263-(2-Oxo-tetrahydropyrimidin-1-yl)propionaldehydeYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(3,3-diethoxypropyl)tetrahydropyrimidin-2-one (1 g, 4.35 mmole), and 1.0 g Dowex 50W2-200 ion exchange resin in 3% aqueous tetrahydrofuran (30 mL) was heated under reflux for 24 hours. The mixture was filtered, the filtrate was concentrated and the residue dissolved in dichloromethane (30 mL), dried with magnesium sulfate, and concentrated to give 3-(2-oxo-tetrahydropyrimidin-1-yl)propionaldehyde (0.46 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionthe residue dissolved in dichloromethane (30 mL)
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-547d7a6d9ed2433382c81a9e0b373035
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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