2-Butyl-1,2-dihydro-4-oxo-6-quinazolinecarboxaldehyde → HCID 178441854, compound

HRID 1974933Notes

Reaction equation

HRID 1974933 reaction equation
[CH2:1]([CH:5]1[NH:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:16]=[O:17])[CH:11]=2)[NH:6]1)[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 191008472-Butyl-1,2-dihydro-4-oxo-6-quinazolinecarboxaldehydeHCID 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-1,2-dihydro-4-oxo-6-quinazolinecarboxaldehyde in 100 ml of tetrahydrofuran, cooled at 0° C., is added 13.0 ml of 2.0 M phenyllithium and stirring continued 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. CI MASS SPEC 309(MH+).

Workup

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

Sources & evidence

ORD record
ord-4fa1ee90765d4242bee4c6959aee9883
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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