N-Methylcyclohexylamine → 6-(cyclohexyl(methyl)amino)-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946723Notes

Reaction equation

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]=2[CH3:18])=[O:9])[CH:3]=1.[CH3:19][NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH:21]1([N:20]([CH3:19])[C:2]2[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=3[CH3:18])=[O:9])[CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 2

HCID 7514N-Methylcyclohexylamine

HCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide2×

Product 1

HCID 251827596-(cyclohexyl(methyl)amino)-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

Procedure

Following the general method as outlined in Example 20, starting from 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 8) and N-methylcyclohexylamine (Aldrich), the title compound was obtained as a yellow solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record: ord-be91b69cc54c4366a1f6e9468f6184d1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399448B2

Reaction notes

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