Methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy-6-dimethylaminopicolinate → Methyl 3-[(4,6-dimethoxypyrimdin-2-yl)oxy]-6-methylaminopicolinate

HRID 1653652Notes

Reaction equation

HRID 1653652 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[C:13]([C:21]([O:23][CH3:24])=[O:22])=[N:14][C:15]([N:18](C)[CH3:19])=[CH:16][CH:17]=2)[N:4]=1>C(Cl)(Cl)Cl>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:13]([C:21]([O:23][CH3:24])=[O:22])=[N:14][C:15]([NH:18][CH3:19])=[CH:16][CH:17]=2)[N:6]=1

Participants

3

Reactant 1

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

Product 1

HCID 15239972Methyl 3-[(4,6-dimethoxypyrimdin-2-yl)oxy]-6-methylaminopicolinateYield 10.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a photoreaction flask having a capacity of 1 l, 20.0 g (60 mmol) of methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(N,N-dimethylamino)picolinate and 1,300 ml of chloroform were charged and irradiated by a 400 W high pressure mercury lamp for 24 hours. Chloroform was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate=6:1 to 3:7) to obtain the desired product.

Workup

  1. customInto a photoreaction flask having
  2. customirradiated by a 400 W high pressure mercury lamp for 24 hours
  3. distillationChloroform was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate=6:1 to 3:7)

Sources & evidence

ORD record
ord-9402b97f070f468f9a1b485b2aa9d881
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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