4-Hydroxyxylidine → 6-(cyclohexylamino)-N-(4-hydroxy-2,3-dimethylphenyl)pyrimidine-4-carboxamide

HRID 1746695Notes

Reaction equation

HRID 1746695 reaction equation
[CH:1]1([NH:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[C:19]=1[CH3:26]>ClCCl>[CH:1]1([NH:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[C:19]=3[CH3:26])=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 765424-HydroxyxylidineHCID 594470756-(Cyclohexylamino)pyrimidine-4-carboxylic acid2×

Product 1

HCID 251827476-(cyclohexylamino)-N-(4-hydroxy-2,3-dimethylphenyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general method as outlined in Example 1, starting from 6-(cyclohexylamino)pyrimidine-4-carboxylic acid (Intermediate 4) and 4-amino-2,3-xylenol (TCI), the title compound was obtained as a white solid after trituration in dichloromethane. 1H NMR (300MHz, DMSO-d6) δ [ppm] 9.91 (1H, s), 9.20 (1H, s), 8.50 (1H, s), 7.73 (1H, d, J=8.0 Hz), 7.18 (1H, d, J=8.5 Hz), 7.12 (1H, s), 6.65 (1H, d, J=8.5 Hz), 3.87 (1H, m), 2.07 (3H, s), 2.06 (3H, s), 1.91-1.61 (5H, m), 1.56-1.15 (5H, m). MS (ESI): 341.1. HPLC (Condition A): Rt 3.02 min (HPLC purity 77.8%).

Sources & evidence

ORD record
ord-6f4534b9e22a4ba7acebde65269b2e19
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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