Dimethylformamide → Methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy-6-phenylpicolinate

HRID 274876Notes

Reaction equation

HRID 274876 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10]([OH:17])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22](S(C)(=O)=O)[N:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([O:17][C:10]2[C:11]([C:13]([O:15][CH3:16])=[O:14])=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15790533Methyl 3-hydroxy-6-phenylpicolinate

Product 1

HCID 15790534Methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy-6-phenylpicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g (4.4 mmol) of methyl 6-phenyl-3-hydroxypicolinate, 0.8 g (4 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.6 g (4 mmol) of potassium carbonate were added to 20 ml of DMF, and were reacted at 80° C. for 0.5 hour. After the reaction, the reaction content was poured into water, and was extracted with ethyl acetate. The organic layer thus obtained was washed with water and a saturated salt water, dried and treated with an appropriate amount of Florisil. Ethyl acetate was then distilled off under reduced pressure, and the residue was crystallized by adding 20 ml of hexane thereto and allowing to stand for 3 days. The crystal thus obtained was washed with hexane/isopropyl ether to obtain an aimed compound.

Workup

  1. customwere reacted at 80° C. for 0.5 hour
  2. customAfter the reaction
  3. extractionwas extracted with ethyl acetate
  4. customThe organic layer thus obtained
  5. washwas washed with water
  6. dry with materiala saturated salt water, dried
  7. additiontreated with an appropriate amount of Florisil
  8. distillationEthyl acetate was then distilled off under reduced pressure
  9. customthe residue was crystallized
  10. additionby adding 20 ml of hexane
  11. customThe crystal thus obtained
  12. washwas washed with hexane/isopropyl ether

Sources & evidence

ORD record
ord-ff321ed8b11b4230b007eb56c4379e41
Source dataset
uspto-grants-1995_02
Patent number
US05391537

Reaction notes

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