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

HRID 1946721

Reaktionsgleichung

Reaktionsgleichung von HRID 1946721
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.ClC1N=CN=C([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=2)=O)C=1.C(N(CC)CC)C.CNC1CCCCC1>C1COCC1>[CH:29]1([N:28]([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)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamideHCID 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-985423f63df048219802cd1a00ee8ba9
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399448B2

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