Carbon Dioxide → 4(1H)-Quinazolinone

HRID 1689998Notes

Reaction equation

HRID 1689998 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=O)=[O:8].[Li]C(C)(C)C.C(=O)=O>C1COCC1.CCOC(C)=O>[CH:1]1[CH:2]=[CH:3][C:4]2[N:12]=[CH:10][NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 64048QuinazolinedioneHCID 178418306HCID 178418306, compound

Product 1

HCID 1354087534(1H)-QuinazolinoneYield 136.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

The quinazoline 1 (1.5 g, 3.0 mmol) was dissolved in THF (150 mL). After cooling to −78° C., t-BuLi (1.7 M in heptane, 1.76 mL) was added dropwise. After stirring for 10 min at −78° C., CO2 (crushed) was added to the solution, then warmed up to RT and stirred for 30 min. Quenched the reaction with H2O (100 mL), diluted with EtOAc (100 mL), The organic layer was dried, concentrated, purified by flash chromatography (1%-10% MeOH/DCM) to obtain 2 (600 mg, 43% yield).

Workup

  1. temperaturewarmed up to RT
  2. stirringstirred for 30 min
  3. customQuenched
  4. customthe reaction with H2O (100 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. custompurified by flash chromatography (1%-10% MeOH/DCM)

Sources & evidence

ORD record
ord-ecd7959c1d424f219dd4666f8e58035e
Source dataset
uspto-grants-2012_04
Patent number
US08153642B2

Reaction notes

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