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

HRID 900656Notes

Reaction equation

HRID 900656 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-d35814e02cea4f1d934594e5c3d02ca9
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Reaction notes

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