N-Ethyl cyclohexylamine → 6-(cyclohexyl(ethyl)amino)-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946727Notes

Reaction equation

HRID 1946727 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.[CH2:19]([NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:20]>>[CH:22]1([N:21]([CH2:19][CH3:20])[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)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 21609N-Ethyl cyclohexylamineHCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide2×

Product 1

HCID 251827636-(cyclohexyl(ethyl)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-ethylcyclohexylamine (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-776a83e431f44fcdb17c6e502ba312b0
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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