Citric Acid → HCID 15240000, compound

HRID 1653656Notes

Reaction equation

HRID 1653656 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]([O:11]C)=[O:10])[C:6]([OH:13])=[CH:5][CH:4]=1.CS([C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CS(C)=O>[CH3:27][O:26][C:20]1[CH:21]=[C:22]([O:24][CH3:25])[N:23]=[C:18]([O:13][C:6]2[C:7]([C:9]([OH:11])=[O:10])=[N:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=2)[N:19]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15240002HCID 15240002, compound

Product 1

HCID 15240000HCID 15240000, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

10.5 mg (0.0576 mmol) of methyl 6-methylamino-3-hydroxypicolinate, 11.6 mg (0.0532 mmol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine, 8.8 mg (0.637 mmol) of potassium carbonate and 0.5 ml of dry dimethylsulfoxide were mixed. The mixture was stirred at room temperature for 5 hours, and then a 10% potassium hydroxide aqueous solution (corresponding to 90 mg, 0.160 mmol) was added thereto. The mixture was reacted at room temperature for one hour, and then 2.0 ml of water was added to the reaction mixture. Further, 1.0 ml of a 10% citric acid aqueous solution was added thereto, and the mixture was left to stand, whereby crystals precipitated. After being thoroughly precipitated, the crystals were filtered under suction and washed with water. The crystals were dried to obtain 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-methylaminopicolinic acid.

Workup

  1. customThe mixture was reacted at room temperature for one hour
  2. waitthe mixture was left
  3. customwhereby crystals precipitated
  4. customAfter being thoroughly precipitated
  5. filtrationthe crystals were filtered under suction
  6. washwashed with water
  7. customThe crystals were dried

Sources & evidence

ORD record
ord-178a15fe1491408a9a749b7017489264
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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