Water → HCID 178441858, compound

HRID 1975446Notes

Reaction equation

HRID 1975446 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[N:20]=1)=[CH:17][C:16]([C:22](OC)=[O:23])=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH3:10].O>O1CCCC1>[CH2:7]([C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[N:20]=1)=[CH:17][C:16]([CH2:22][OH:23])=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride3×HCID 178441861methyl 2-butyl-4-oxo-1H-quinazoline-6-carboxylate

Product 1

HCID 178441858HCID 178441858, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.013 g of lithium aluminum hydride in 5.0 ml of tetrahydrofuran is added 0.100 g of methyl 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxylate followed by stirring at room temperature for 5 hours. An additional 20 mg of lithium aluminum hydride is added and stirring continued for 18 hours. An additional 20 mg of lithium aluminum hydride is added and stirring continued for an additional 8 hours. The reaction mixture is poured into 75 ml of water and extracted with ethyl acetate. The extract is evaporated in vauco to a residue which is stirred with acetone and filtered to give 0.040 g of the desired product as a white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. stirringstirring
  4. waitcontinued for an additional 8 hours
  5. extractionextracted with ethyl acetate
  6. customThe extract is evaporated in vauco to a residue which
  7. stirringis stirred with acetone
  8. filtrationfiltered

Sources & evidence

ORD record
ord-32cfab9d3905401e8378159d82d0135a
Source dataset
uspto-grants-1994_02
Patent number
US05286729

Reaction notes

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