Lithium Hydroxide → HCID 59484906, compound

HRID 1408394Notes

Reaction equation

HRID 1408394 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[N:20]=[CH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][N:16]=3)[CH:12]=[CH:13][CH:14]=2)[N:6]=[C:5]([C:26]2[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=2)[CH:4]=[CH:3]1.[OH-].[Li+]>C1COCC1.O>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[N:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]=3)[CH:12]=[CH:13][CH:14]=2)[N:6]=[C:5]([C:26]2[CH:27]=[C:28]([F:34])[C:29]([F:33])=[C:30]([F:32])[CH:31]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59484892HCID 59484892, compound

Product 1

HCID 59484906HCID 59484906, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.4 g (7.29 mmol) of ethyl 2-{3-[6-oxo-3-(3,4,5-trifluorophenyl)-6H-pyridazin-1-ylmethyl]phenyl}pyrimidine-5-carboxylate are dissolved in 300 ml of THF and 30 ml of water, and 713 mg (29.2 mmol) of lithium hydroxide are added. The reaction mixture is refluxed for 4 h and cooled to room temperature, and the organic solvent is removed by distillation in a rotary evaporator. 300 ml of water and 30 ml of THF are added to the residue, and conc. HCl is slowly added dropwise to this solution with stirring until the reaction is strongly acidic. The precipitate formed is filtered off with suction, washed with copious water and dried in a vacuum drying cabinet.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 h
  2. customthe organic solvent is removed by distillation in a rotary evaporator
  3. addition300 ml of water and 30 ml of THF are added to the residue, and conc. HCl
  4. additionis slowly added dropwise to this solution
  5. customThe precipitate formed
  6. filtrationis filtered off with suction
  7. washwashed with copious water
  8. customdried in a vacuum
  9. customdrying cabinet

Sources & evidence

ORD record
ord-c89823443399468aadd03bda5b102824
Source dataset
uspto-grants-2014_12
Patent number
US08921357B2

Reaction notes

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