3-Bromopropionaldehyde dimethylacetal → HCID 57927656, compound

HRID 889169Notes

Reaction equation

HRID 889169 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[NH:4][C:3]1=[O:13].CC(C)([O-])C.[K+].[CH3:20][O:21][CH:22]([O:26][CH3:27])[CH2:23][CH2:24]Br>CO>[CH3:20][O:21][CH:22]([O:26][CH3:27])[CH2:23][CH2:24][N:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11](=[O:12])[N:2]([CH3:1])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 1189323-Bromopropionaldehyde dimethylacetalHCID 13357775HCID 13357775, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 57927656HCID 57927656, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After suspending 3-methyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dione (CAS 85458-77-1) (500 mg) in methanol (10 ml), potassium tert-butoxide (342 mg) was added and the mixture was stirred at room temperature for 30 minutes. After then adding 3-bromopropionaldehyde dimethylacetal (0.57 ml), the mixture was heated to reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (235 mg).

Workup

  1. additionwas added
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added to the residue, and extraction
  5. washThe organic layer was washed with water and brine in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae507fad587e41dd8543365848490105
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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