Sodium Iodide → methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(N-methyl-N-cyclohexylamino)picolinate

HRID 1653633Notes

Reaction equation

HRID 1653633 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[N+:14]([O-])[C:13]=2[C:19]([O:21][CH3:22])=[O:20])[N:4]=1.[CH3:23][N:24]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)C(Cl)=O.[I-].[Na+].C(N(C(C)C)CC)(C)C>O.C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:13]([C:19]([O:21][CH3:22])=[O:20])=[N:14][C:15]([N:24]([CH3:23])[CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:16][CH:17]=2)[N:4]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 14425903methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate N-oxideHCID 15209947N-cyclohexyl-N-methylcarbamoyl chloride

Product 1

HCID 15239966methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(N-methyl-N-cyclohexylamino)picolinateYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

11.0 g (36 mmol) of methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate N-oxide, 9.5 g (54 mmol) of N-methyl-N-cyclohexylcarbamoyl chloride, 10.5 g (70 mmol) of sodium iodide and 9.0 g (70 mmol) of diisopropylethylamine were added to 150 ml of acetonitrile and reacted at a temperature of from 60° to 70° C. for one hour. Water was added to the reaction solution, and the organic layer was extracted with ethyl acetate, dried and concentrated. The obtained oily product was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the desired product.

Workup

  1. customreacted at a temperature of from 60° to 70° C. for one hour
  2. extractionthe organic layer was extracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained oily product was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b1f5c5f1ed714a658c4aa9bbebb447b9
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

Loading…