Methyl Ethyl Ketone → HCID 15239990, compound

HRID 1653641Notes

Reaction equation

HRID 1653641 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)=[CH:4][CH:3]=1.Cl.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](Cl)=[O:31].C(=O)([O-])[O-].[K+].[K+].CCC(C)=O>O>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([NH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)=[CH:4][CH:3]=1)=[O:31]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 135033Picolinoyl Chloride HydrochlorideHCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

Product 1

HCID 15239990HCID 15239990, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 g (6.5 mmol) of methyl 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate, 1.2 g (6.5 mmol) of picolinoyl chloride hydrochloride and 2.0 g (14.8 mmol) of potassium carbonate were added to 30 ml of MEK, and the mixture was refluxed for 6 hours under stirring. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was distilled off to obtain crude crystals. The crude crystals were washed with diisopropyl ether-ethyl acetate to obtain the desired product as colorless needle-like crystals.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customto obtain crude crystals
  8. washThe crude crystals were washed with diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-a16ea183a1d14f02b5e26277ceefe57b
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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