Dimethylformamide → HCID 59853028, compound

HRID 2373936Notes

Reaction equation

HRID 2373936 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N: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].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:8][C:6]1[CH:7]=[C:2]([O:19][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[F:9])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 59853028HCID 59853028, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,6-dichloropyrimidine (Aldrich, 0.74 g, 5.0 mmol), 2-fluoro-4-nitrophenol (Aldrich, 0.79 g, 5.0 mmol) and DMF (10 ml) was treated with potassium carbonate (0.72 g, 5.2 mmol) and heated at 80° C. for 3 h. The mixture was cooled, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried (MgSO4), and concentrated to give the crude product as a yellow solid. The crude product was triturated with isopropyl ether to give 4-chloro-6-(2-fluoro-4-nitrophenoxy)pyrimidine as a yellow solid (1.3 g, 94%). 1H NMR (DMSO-d6) δ 8.80 (s, 1H), 8.51 (dd, 1H, J=8.6, 2.5 Hz), 8.31 (d, 1H, J=9.1 Hz), 7.87 (d, 1H, J=9.1 Hz), 7.84 (s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give the crude product as a yellow solid
  8. customThe crude product was triturated with isopropyl ether

Sources & evidence

ORD record
ord-77656f45a03548a391cd59615f2d333a
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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