HCID 178441857, compound → HCID 178441854, compound

HRID 487058Notes

Reaction equation

HRID 487058 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:16]=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:16]([OH:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178441857HCID 178441857, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 178441854HCID 178441854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2.00 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde in 100 ml of tetrahydrofuran, cooled at 0° C., is added 13.0 ml of 2.0M phenyllithium and stirring continued is for 1 hour. The cooling is removed and the reaction allowed to reach room-temperature followed by an additional 30 minutes at room temperature. The reaction is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer is dried, evaporated to a residue, which is purified by chromatography on silica gel by elution with 0.25:100 methanol-chloroform to give 0.932 g of the desired product.

Workup

  1. customThe cooling is removed
  2. waitfollowed by an additional 30 minutes at room temperature
  3. additionThe reaction is diluted with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. customThe organic layer is dried
  6. customevaporated to a residue, which
  7. customis purified by chromatography on silica gel by elution with 0.25:100 methanol-chloroform

Sources & evidence

ORD record
ord-04d2c50aa10845d8a77e85ba65eaa0f4
Source dataset
uspto-grants-1994_03
Patent number
US05294611

Reaction notes

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