N-Methylcyclohexylamine → 6-(cyclohexyl(methyl)amino)-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

HRID 1746704

Reaktionsgleichung

Reaktionsgleichung von HRID 1746704
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2C)=[O:9])[CH:3]=1.C(N(CC)CC)C.[CH3:26][NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH:28]1([N:27]([CH3:26])[C:2]2[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)=[O:9])[CH:3]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

5

Edukt 3

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

Produkt 1

HCID 251827586-(cyclohexyl(methyl)amino)-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide, Intermediate 7 (75.0 mg; 0.30 mmol) in THF (4 mL) was treated with triethylamine (42 μl; 0.30 mmol) and N-methylcyclohexylamine (Aldrich, 43 μl; 0.33 mmol). The reaction mixture was stirred for 24 h. The solvents were removed in vacuo, then the crude product was purified by column chromatography (silica), eluting with cyclohexane containing an increasing amount of EtOAc. The title compound was obtained as a yellow solid.

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by column chromatography (silica)
  3. washeluting with cyclohexane containing an increasing amount of EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5cbaae8696f74418969f2a1775b820da
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150519B2

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