Piconol → 4-tert-butyl-N-{5-(3-methoxyphenoxy)-6-(2-pyridinylmethoxy)pyrimidin-4-yl}benzenesulfonamide

HRID 1082260Notes

Reaction equation

HRID 1082260 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[C:30]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)=[C:29](Cl)[N:28]=[CH:27][N:26]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[Cl-].[NH4+]>CC(N(C)C)=O>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([S:21]([NH:24][C:25]2[C:30]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)=[C:29]([O:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:28]=[CH:27][N:26]=2)(=[O:22])=[O:23])=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 11474PiconolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 15391273p-t-butyl-N-[6-chloro-5-(m-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

Product 1

HCID 153912714-tert-butyl-N-{5-(3-methoxyphenoxy)-6-(2-pyridinylmethoxy)pyrimidin-4-yl}benzenesulfonamideYield 94.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of pyridine-2-methanol (130 mg) in dimethylacetamide (0.5 ml) is added gradually with stirring sodium hydride (62.7% dispersion-type, 60 mg) under ice-cooling, and thereto is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (100 mg). The mixture is reacted at 100° C. for 30 minutes, and cooled. The pH value of the mixture is adjusted to pH 8 with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and concentrated to dryness under reduced pressure. The residue is crystallized from ethyl acetate to give 4-tert-butyl-N-{5-(3-methoxyphenoxy)-6-(2-pyridinylmethoxy)pyrimidin-4-yl}benzenesulfonamide (110 mg) as crystals.

Workup

  1. temperaturecooling
  2. customThe mixture is reacted at 100° C. for 30 minutes
  3. temperaturecooled
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe extract is washed
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-59baafb44d994d2a8e27745a9ee5f8f9
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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