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

HRID 274875Notes

Reaction equation

HRID 274875 reaction equation
[CH3:1][N:2]([C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([OH:14])=[CH:6][CH:5]=1)[CH3:3].[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19](S(C)(=O)=O)[N:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([O:14][C:7]2[C:8]([C:10]([O:12][CH3:13])=[O:11])=[N:9][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15767145HCID 15767145, compound

Product 1

HCID 15767146Methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy-6-dimethylaminopicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.4 g (7 mmol) of methyl 6-(N,N-dimethylamino)-3-hydroxypicolinate, 1.6 g (7 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.6 g (4 mmol) of potassium carbonate were added to 100 ml of dimethylformamide (DMF), and were reacted at 90° C. for 2 hours. After the reaction, the reaction content was poured into water, and was extracted with diethyl ether, and then washed with water, dried and concentrated to obtain an oily product which was thereafter crystallized with isopropyl ether. The crystal thus obtained was recrystallized with ethyl acetate/n-hexane to obtain an aimed product.

Workup

  1. customwere reacted at 90° C. for 2 hours
  2. customAfter the reaction
  3. extractionwas extracted with diethyl ether
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customto obtain an oily product which
  8. customwas thereafter crystallized with isopropyl ether
  9. customThe crystal thus obtained
  10. customwas recrystallized with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-65c16082835045e5b37cefcb6b892fbf
Source dataset
uspto-grants-1995_02
Patent number
US05391537

Reaction notes

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