Cycloheptylamine → 6-(cycloheptylamino)-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1746708Notes

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.[CH:19]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([NH:26][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)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Reactant 2

HCID 2899Cycloheptylamine

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

Product 1

HCID 251827616-(cycloheptylamino)-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 cycloheptylamine (Aldrich), the title compound was obtained as a beige solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record: ord-7f488fe3e27c463f9d7cb4e02dc3cea1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

Loading…