HCID 178418507, compound → HCID 178458208, compound

HRID 1742184Notes

Reaction equation

HRID 1742184 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].[CH:18]([Mg]Br)=[CH2:19]>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])[CH:18]=[CH2:19])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178418507HCID 178418507, compoundHCID 178441857HCID 178441857, compound

Product 1

HCID 178458208HCID 178458208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 10.00 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde in 350 ml of tetrahydrofuran, cooled to 0° C. is added 130.43 ml of 1.0M vinylmagnesium bromide in tetrahydrofuran over 15 minutes. The reaction mixture is stirred at 0° C. for 30 minutes. The reaction mixture is quenched at 0° C. with 50 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer is dried (Na2SO4) and concentrated in vacuo to afford a residue which is purified by column chromatography on silica gel using 1:1 ethyl acetate-hexane to give 4.81 g of the desired product, as a white solid, MP 141° C.

Workup

  1. customThe reaction mixture is quenched at 0° C. with 50 ml of saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a residue which
  6. customis purified by column chromatography on silica gel using 1:1 ethyl acetate-hexane

Sources & evidence

ORD record
ord-1e44a5f92a794bf6bc35d3587ce5a20e
Source dataset
uspto-grants-1994_08
Patent number
US05338736

Reaction notes

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