Potassium Hydroxide → HCID 18619192, compound

HRID 1862241Notes

Reaction equation

HRID 1862241 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[OH:22].Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1.[OH-].[K+]>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[O:22][C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 796132-Chloro-3-nitropyridineHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 18619192HCID 18619192, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

11.8 g of 2chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol and 5.2 g of 2-chloro-3-nitropyridine were dissolved in 10 ml of toluene, to this were added 2.3 g of potassium hydroxide and 56 mg of 18-crown-6, and the mixture was stirred for 3 hours at 90° C. The reaction solution was cooled to room temperature, then the solvent was distilled off, and the residue was poured into ice water, and the precipitated crystals were collected by filtration to obtain 11.5 g of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-nitropyridine.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off
  3. additionthe residue was poured into ice water
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-19529d284bd64bc7889b8e795768410e
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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