Dimethylformamide → Methyl 6-(acetylamino)-3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-2-pyridinecarboxylate

HRID 1653651Notes

Reaction equation

HRID 1653651 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([OH:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20](S(C)(=O)=O)[N:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([O:15][C:20]2[N:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:18]([O:17][CH3:16])[N:19]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15239999Methyl 6-acetamido-3-hydroxypyridine-2-carboxylate

Product 1

HCID 15767151Methyl 6-(acetylamino)-3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-2-pyridinecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.78 g (3.7 mmol) of the obtained methyl 6-acetylamino-3-hydroxypicolinate, 0.81 g (3.7 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.51 g (3.7 mmol) of potassium carbonate were added to 50 ml of DMF, and the mixture was reacted at 80° C. for two hours. After completion of the reaction, the reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water, dried and concentrated. The oily product thereby obtained was purified by column chromatography to obtain methyl 6-acetylamino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate.

Workup

  1. customthe mixture was reacted at 80° C. for two hours
  2. customAfter completion of the reaction
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe oily product thereby obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-97fdc116624447b0bba2758fd538da48
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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