Water → HCID 178441858, compound

HRID 487059Notes

Reaction equation

HRID 487059 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 vacuo 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 vacuo to a residue which
  7. stirringis stirred with acetone
  8. filtrationfiltered

Sources & evidence

ORD record
ord-e9c42e34f08b46dd9630bb3970d6ed53
Source dataset
uspto-grants-1994_03
Patent number
US05294611

Reaction notes

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