Potassium Carbonate → Methyl (2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)acetate

HRID 2060646Notes

Reaction equation

HRID 2060646 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C)C=O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][C:15]1[N:14]=[CH:13][N:12]=[C:11]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:16]=1)#[N:5]

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 119072-HydroxybenzonitrileHCID 709434,6-DichloropyrimidineHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 11187557Methyl (2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under the dried nitrogen atmosphere, to a reaction flask were added 540 mL of dried N,N-dimethylformamide, 26.2 g of 2-hydroxybenzonitrile, 29.8 g of 4,6-dichloropyrimidine and 27.6 g of anhydrous potassium carbonate, and this mixture is heated under stirring to 100. degree. C. to be followed by reacting for 3 hrs. Then, 34.9 g of methyl 2-hydroxyphenylacetate and 13.8 g of anhydrous potassium carbonate were added and the temperature was increased to 120. degree. C. The reaction went on under stirring for 5 hrs. Afterwards, N,N-dimethylformamide was recovered by concentrating the reaction mixture under reduced pressure, 150 mL of toluene and 100 mL of water were added to the residue to dissolve the solid under stirring. The solution was left to stand still for separation of an organic phase and an aqueous phase. The organic phase was concentrated to obtain .a solid crude product of methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxy)phenyl)acetate. After purification, 54 g of amber solid was obtained from the crude product with a yield of 75%.

Workup

  1. temperaturethis mixture is heated
  2. temperaturethe temperature was increased to 120
  3. stirringunder stirring for 5 hrs
  4. customAfterwards, N,N-dimethylformamide was recovered
  5. concentrationby concentrating the reaction mixture under reduced pressure, 150 mL of toluene and 100 mL of water
  6. additionwere added to the residue
  7. dissolutionto dissolve the solid
  8. stirringunder stirring
  9. waitThe solution was left
  10. customto stand still for separation of an organic phase
  11. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-9fecff6bffcf4b4780f37263c1ab2fea
Source dataset
uspto-grants-2012_10
Patent number
US08278445B2

Reaction notes

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