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

HRID 2301393Notes

Reaction equation

HRID 2301393 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-44cb2e5cf2394d63bcd667a346052fc4
Source dataset
uspto-grants-2002_12
Patent number
US06500822B2

Reaction notes

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