Water → HCID 21865086, compound

HRID 857638Notes

Reaction equation

HRID 857638 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.[C:18]([NH:21][C:22]1[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[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:28][C:24]3[CH:23]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:27]=[CH:26][CH:25]=3)[CH:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 121243-HydroxyacetanilideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 21865086HCID 21865086, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (520 mg, 2.0 mmol), 3-acetamidophenol (320 mg, 2.1 mmol, Aldrich) and K2CO3 (368 mg, 2.7 mmol) in DMF (10 mL) was heated at 80° C. for 8 h. The mixture was allowed to cool to room temperature, poured into H2O, extracted with EtOAc and the combined organic layers were evaporated onto SiO2. Purification by flash silica gel chromatography with EtOAc/hexanes (0:1→2:3) as eluant gave the title compound as a white amorphous solid. Mp: 202–205° C. MS (ESI, pos ion.) m/z: 374 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc
  3. customthe combined organic layers were evaporated onto SiO2
  4. customPurification by flash silica gel chromatography with EtOAc/hexanes (0:1→2:3) as eluant

Sources & evidence

ORD record
ord-da41f2a78d2c4ea396137c50d1f8ff0e
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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