HCID 178418255, compound → HCID 178441844, compound

HRID 486503Notes

Reaction equation

HRID 486503 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][CH2:15][CH2:16][CH3:17])=[N:8][C:7]2=[O:18])(=[O:3])[CH3:2].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.[Cl-].[NH4+]>[CH2:14]([C:9]1[NH:10][C:11]2[C:6]([C:7](=[O:18])[N:8]=1)=[CH:5][C:4]([C:1]([OH:3])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:2])=[CH:13][CH:12]=2)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 178418255HCID 178418255, compoundHCID 178441846HCID 178441846, compound

Product 1

HCID 178441844HCID 178441844, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2.08 g of 6-acetyl-2-butyl-4(1H)-quinazolinone in 80 ml of tetrahydrofuran is added dropwise at room temperature 14.2 ml of 3.0M phenylmagnesium bromide. The reaction mixture is stirred at room temperature overnight then diluted with aqueous ammonium chloride and extracted with chloroform. The organic layer is dried and evaporated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 1:1 ethyl acetate-hexanes to give 0.535 g of the desired product as a solid. Cl MASS SPEC 323 (MH+).

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer is dried
  3. customevaporated in vacuo to a residue which
  4. customis purified by column chromatography on silica gel by elution with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-ab642e6f194440a7a0e7cbb0454941ed
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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