Sodium hydride → N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

HRID 1062716Notes

Reaction equation

HRID 1062716 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][OH:24])[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:34][C:35]1[CH:36]=[N:37][C:38](Cl)=[N:39][CH:40]=1.CC(N(C)C)=O>O1CCCC1.O>[Br:34][C:35]1[CH:36]=[N:37][C:38]([O:24][CH2:23][CH2:22][O:21][C:17]2[C:16]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:15]([NH:14][S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=3)(=[O:12])=[O:13])[N:19]([CH3:20])[N:18]=2)=[N:39][CH:40]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 6066655-Bromo-2-chloropyrimidineHCID 222820434-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Product 1

HCID 9894949N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamideYield 35.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Example 2) (25 mg) in tetrahydrofuran (2 ml) at room temperature under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 4.5 mg) and the mixture was stirred for 5 minutes. To the mixture was added 5-bromo-2-chloropyrimidine (Liquid Crystals, 1993, 14(3), 741) (12 mg) and the reaction was stirred for 30 minutes after which dimethyl acetamide (0.5 ml) was added to give a homogenous mixture. After further stirring for 3 hrs the reaction was diluted with water (20 ml) and extracted with ethyl acetate (20 ml). The organic fraction was dried over magnesium sulfate, filtered concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with dichloromethane:ether (1:1) to yield the title compound as a white solid (12 mg).

Workup

  1. additionwas added
  2. customto give a homogenous mixture
  3. stirringAfter further stirring for 3 hrs the reaction
  4. extractionextracted with ethyl acetate (20 ml)
  5. dry with materialThe organic fraction was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica (10 g)
  9. washeluted with dichloromethane:ether (1:1)

Sources & evidence

ORD record
ord-b514088e037d4b2f9a71fed4582c04cf
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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