Potassium Carbonate → 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate

HRID 2268

Reaction equation

HRID 2268 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:7]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1.Cl[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>[Cl-].[NH4+]>[OH2:5].[C:22]([C:19]1[CH:18]=[CH:17][C:16]([S:13]([NH:12][C:8]2[C:7]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)=[C:6]([O:5][CH2:4][CH2:3][NH:2][C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[N:11]=[CH:10][N:9]=2)(=[O:15])=[O:14])=[CH:21][CH:20]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 744042-ChloropyrimidineHCID 67654095N-{6-(2-aminoethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide hydrochloride

Product 1

HCID 196894824-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrateYield 161.1%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Compound A (150 mg), 2-chloropyrimidine (61 mg), potassium carbonate (122 mg) and dimethylacetamide (1.5 ml) is heated with stirring at 100° C. for three days. The reaction solution is diluted with aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract is washed and dried. The solvent is evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1) and further recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate (135 mg) as crystals.

Workup

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. customThe solvent is evaporated
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1)
  8. customfurther recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1febdfb0ad8749368c5d7d698e941579
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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