Dimethylformamide → HCID 59853046, compound

HRID 2373956Notes

Reaction equation

HRID 2373956 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([O:19][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[F:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 775312,4-Dichloropyrimidine

Product 1

HCID 59853046HCID 59853046, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dichloropyrimidine (Aldrich, 0.74 g, 5.0 mmol), 2-fluoro-4-nitrophenol (Avacado, 0.79 g, 5.0 mmol), K2CO3 (0.76 g, 5.5 mmol), and DMF (50 mL) was heated at 100° C. for 2 h. The mixture was cooled and diluted with saturated NaHCO3 solution (100 mL) and extracted with EtOAc. The EtOAc extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give a mixture of the 2-phenoxy- and 4-phenoxypyrimidine regioisomers as a yellow solid. The regioisomers were separated by flash chromatography using 10-40% EtOAc in hexanes as the eluent to give the title compound (0.71 g, 53%) as a white solid. 1H NMR (DMSO-d6) δ 8.76 (dd, 1H, J=6.0, 1.6 Hz), 8.43 (dt, 1H, J=9.8, 2.2 Hz), 8.23 (dd, 1H, J=8.8, 1.6 Hz), 7.80 (dt, 1H, J=9.8, 2.2 Hz), 7.48 (dd, 1H, J=6.0, 2.2 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give
  8. customThe regioisomers were separated by flash chromatography

Sources & evidence

ORD record
ord-33c7185ba5854b4cbf1b6aaa3fec5017
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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