Dimethylformamide → Methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-methylnicotinate

HRID 1770076Notes

Reaction equation

HRID 1770076 reaction equation
[OH:1][C:2]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1.CN(C)C=O>O>[CH3:29][O:28][C:22]1[CH:23]=[C:24]([O:26][CH3:27])[N:25]=[C:20]([O:1][C:2]2[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 51523232-Chloro-4,6-dimethoxypyrimidineHCID 178497913HCID 178497913, compound

Product 1

HCID 20095253Methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-methylnicotinateYield 8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (0.03 mol) of methyl 2-hydroxy-6-methylnicotinate, 5.0 g (0.03 mol) of potassium carbonate, 5.7 g (0.03 mol) of 2-chloro-4,6-dimethoxypyrimidine and 50 ml of N,N-dimethylformamide were weighed, and were reacted at 100° C. for 4 hours. The reaction mixture was then poured into water, and was extracted with 100 ml of ethyl acetate. The organic layer was then washed with water and a saturated sodium chloride aqueous solution. After drying with anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.73 g of the aimed product.

Workup

  1. customwere reacted at 100° C. for 4 hours
  2. extractionwas extracted with 100 ml of ethyl acetate
  3. washThe organic layer was then washed with water
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9798b391204444be9315ebb2b3fecfb5
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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