Methyl iodide → 3-[(4-Bromophenyl)methyl]-2-butyl-6-(1-methoxy-1-methylethyl)-4(3H)-quinazolinone

HRID 1654151Notes

Reaction equation

HRID 1654151 reaction equation
[H-].[Na+].I[CH3:4].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]([OH:27])([CH3:26])[CH3:25])[CH:20]=3)[N:15]=[C:14]2[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:8][CH:7]=1>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]([O:27][CH3:4])([CH3:25])[CH3:26])[CH:20]=3)[N:15]=[C:14]2[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200793443-[(4-Bromophenyl)methyl]-2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone

Product 1

HCID 200793433-[(4-Bromophenyl)methyl]-2-butyl-6-(1-methoxy-1-methylethyl)-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.186 g of 60% sodium hydride and 2.90 ml of iodomethane in THF at room temperature is added 1.00 g of 3-[(4-bromophenyl)methyl]-2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone. The reaction mixture is stirred overnight at room temperature and then quenched with ammonium chloride solution and diluted with water. The aqueous layer is extracted with ether and the combined organics are dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chrmoatography eluting with ethyl acetate/hexanes (1:3) to provide the desired product.

Workup

  1. customquenched with ammonium chloride solution
  2. additiondiluted with water
  3. extractionThe aqueous layer is extracted with ether
  4. dry with materialthe combined organics are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chrmoatography
  8. washeluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-f6d0e86337ce48419b24a8c0faafda6f
Source dataset
uspto-grants-1995_04
Patent number
US05405849

Reaction notes

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