Ammonium Chloride → 4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

HRID 1082286

Reaktionsgleichung

Reaktionsgleichung von HRID 1082286
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([CH:38]=[O:39])=[CH:34][N:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.C(O)(C)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([CH2:38][OH:39])=[CH:34][N:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 110280074-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

Produkt 1

HCID 109626374-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamideAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22597222Tetrahydrofuran 2-propanolLösungsmittel

Versuchsvorschrift

To a solution of 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (143 mg) in tetrahydrofuran-isopropanol (4 ml-4 ml) is added sodium borohydride (13 mg) under ice-cooling, and the mixture is reacted for two hours. The mixture is treated with aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1), and crystallized from diethyl ether to give 4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (96 mg).

Aufarbeitung

  1. temperaturecooling
  2. customthe mixture is reacted for two hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
  9. customcrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3d18108b855e4dc5ba8da6ac289909cd
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589478

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