HCID 178441857, compound → HCID 178441854, compound

HRID 486029Notes

Reaction equation

HRID 486029 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-quinazoline-carboxaldehyde in 100 ml of tetrahydrofuran, cooled at 0° C., is added 13.0 ml of 2.0M 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-7f492ab420fd44e881321a1fa249433d
Source dataset
uspto-grants-1994_03
Patent number
US05290780

Reaction notes

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