Potassium Carbonate → Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

HRID 1653653Notes

Reaction equation

HRID 1653653 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.CS([C:17]1[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:17]2[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15239995HCID 15239995, compound

Product 1

HCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinateYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF suspension (50 ml) of 3.0 g (17.8 mmol) of methyl 6-amino-3-hydroxypicolinate, 3.9 g (17.8 mmol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine and 1.23 g (8.9 mmol) of potassium carbonate in a 100 ml round bottomed flask, was stirred at 80° C. for 4 hours. The reaction mixture was poured into ice water and extracted with dichloromethane. The organic layer was washed with water, dried, concentrated and purified by silica gel chromatography (n-hexane/AcOEt=1/1+0.1 MeOH) to obtain 4.43 g (yield: 81.3%) of the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (n-hexane/AcOEt=1/1+0.1 MeOH)

Sources & evidence

ORD record
ord-ffffbb1b42554fd7a349878bd76f0b9a
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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