Sodium hydride → HCID 54162703, compound

HRID 1464344Notes

Reaction equation

HRID 1464344 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[CH2:4][CH3:5].[C:17]([N:36]1[C:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:47]2[CH:54]=[CH:53][C:50]([CH2:51]Br)=[CH:49][CH:48]=2)=[N:39][N:38]=[N:37]1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:3]([C:6]1[N:15]([CH2:51][C:50]2[CH:49]=[CH:48][C:47]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[C:40]3[N:36]([C:17]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:37]=[N:38][N:39]=3)=[CH:54][CH:53]=2)[C:14](=[O:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 1354006282-propyl-4(3H)-quinazolinone

Product 1

HCID 54162703HCID 54162703, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of sodium hydride (60% dispersion in mineral oil, 0.3 g) in DMF (50 ml) was added 2-propyl-4(3H)-quinazolinone (1.0 g) and the mixture was stirred at room temperature for 15 minutes. After addition of 4-[2'-(N-trityltetrazol-5-yl)phenyl]benzyl bromide (5.0 g), the reaction mixture was stirred at room temperature for 19 hours and concentrated to dryness. The residue was extracted with ethyl acetate-water and the organic layer was washed with water, dried and concentrated to dryness. The resulting syrup was purified by column chromatography on silica gel to give a colorless amorphous (2.34 g, 66%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 19 hours
  2. concentrationconcentrated to dryness
  3. extractionThe residue was extracted with ethyl acetate-water
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe resulting syrup was purified by column chromatography on silica gel
  8. customto give a colorless amorphous (2.34 g, 66%)

Sources & evidence

ORD record
ord-2089710900db43d88ae1a2fcd764bb9c
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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