Dimethylformamide → HCID 59853028, compound

HRID 1670188Notes

Reaction equation

HRID 1670188 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-1ef4786e2c3344a59ed3c89ae8e9f707
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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