Sodium hydride → HCID 18931103, compound

HRID 1599026Notes

Reaction equation

HRID 1599026 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[C:22]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])=[C:21]([O:32][CH2:33][CH2:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[N:20]=[C:19](S(C)(=O)=O)[N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>C(O)CO>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[C:22]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])=[C:21]([O:32][CH2:33][CH2:34][O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[N:20]=[C:19]([O:23][CH2:22][CH2:21][OH:32])[N:18]=2)(=[O:14])=[O:15])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18931062HCID 18931062, compound

Product 1

HCID 18931103HCID 18931103, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

##STR149## (1) To ethylene glycol (2 ml) is added sodium hydride (60% dispersion, 125.8 mg). To this mixture is added 4-tert-butyl-N-{5-(2-methoxyphenoxy)-2-methylsulfonyl-6-[2-(tetrahydropyran-2-yloxy)ethoxy]pyrimidin-4-yl}benzene-sulfonamide obtained in Reference Example 10-(2) (500 mg), and the mixture is stirred at room temperature for 18 hours. To the reaction solution is added an aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=1:1) to give 4-tert-butyl-N-{2-(2-hydroxyethoxy)-5-(2-methoxy-phenoxy)-6-[2-(tetrahydropyran-2-yloxy)ethoxy]pyrimidin-4-yl}benzene-sulfonamide (440.5 mg) as a colorless caramel.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe ethyl acetate layer is washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-274a8b278d414fdbbbdd7b22536d5882
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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