2-Aminophenol → HCID 21865318, compound

HRID 858991Notes

Reaction equation

HRID 858991 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].[H-].[Na+]>CN(C=O)C.O>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[NH2:18])[CH:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 58012-AminophenolHCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 21865318HCID 21865318, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.52 g, 2.0 mmol) and 2-aminophenol (0.26 g, 2.4 mmol, Aldrich) in DMF (10 mL) was added sodium hydride (0.09 g, 2.2 mmol, 60% dispersion in mineral oil, Aldrich). The mixture was heated at 50° C. for 2 h, allowed to cool to room temperature and diluted with H2O. The resulting solid was filtered, washed with H2O and dried in vacuum at room temperature for 20 h to afford the title compound as a white powder. Mp: 188° C., MS (ESI, pos. ion) m/z: 332 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with H2O
  4. customdried in vacuum at room temperature for 20 h

Sources & evidence

ORD record
ord-4654e169154e4be087ec683e58f94d89
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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