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

HRID 1946721

Reaction equation

HRID 1946721 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]=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

Participants

6

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamideHCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-985423f63df048219802cd1a00ee8ba9
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Linked notes

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