HCID 178418573, compound → HCID 178441842, compound

HRID 1974929Notes

Reaction equation

HRID 1974929 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].[CH3:19][Mg]Br>O1CCCC1.C(OCC)C>[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])([CH3:19])[CH3:2])=[CH:13][CH:12]=2)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178441846HCID 178441846, compound

Product 1

HCID 178441842HCID 178441842, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.00 g of 6-acetyl-2-butyl-4-(1H)-quinazolinone in 250 ml of dry tetrahydrofuran, cooled to 0° C., is added dropwise 16.4 ml of 3.0M methylmagnesium bromide in diethyl ether. The reaction is stirred at 0° C. for 0.5 hours and then allowed to warm to room temperature followed by quenching with 100 ml of saturated ammonium chloride solution. The mixture is diluted with 50 ml of water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 100:0.25 chloroform-methanol to give 2.75 g of the desired product as a white solid. CI MASS SPEC 261(MH+).

Workup

  1. temperatureto warm to room temperature
  2. customby quenching with 100 ml of saturated ammonium chloride solution
  3. additionThe mixture is diluted with 50 ml of water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash chromatography on silica gel
  10. washeluting with 100:0.25 chloroform-methanol

Sources & evidence

ORD record
ord-bc52a4a940c54c87b0b0855e55efa624
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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