Water → HCID 57927329, compound

HRID 889168Notes

Reaction equation

HRID 889168 reaction equation
[CH3:1][O:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1.[CH3:14][O:15][CH:16]([O:20][CH3:21])[CH2:17][CH2:18]Br.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:15][CH:16]([O:20][CH3:21])[CH2:17][CH2:18][N:12]1[C:11](=[O:13])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[C:3]1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 135995422HCID 135995422, compound

Product 1

HCID 57927329HCID 57927329, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

After dissolving 2-methoxy-5,6,7,8-tetrahydro-3H-quinazolin-4-one (CAS 94815-67-5) (2.0 g) and 3-bromopropionaldehyde dimethylacetal (2.44 g) in N,N-dimethylformamide (30 ml), sodium hydride (60% in oil) (533 mg) was added, and the mixture was stirred at room temperature for 30 minutes and at 100° C. for 5 hours. Water was added to the reaction mixture, 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 (640 mg).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-247d9a3063c04df8b4c3f05121f3f07d
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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