Methanol → HCID 22636403, compound

HRID 2415689Notes

Reaction equation

HRID 2415689 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:10]3[CH:9]2[C:18]2[CH:23]=[CH:22][N:21]=[C:20](SC)[N:19]=2)=[CH:4][CH:3]=1.[CH3:26]O.O[O:29][S:30]([O-:32])=O.[K+]>C1COCC1.O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16](=[O:17])[N:11]3[CH2:12][CH:13]=[CH:14][CH2:15][N:10]3[CH:9]2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:30]([CH3:26])(=[O:32])=[O:29])[N:19]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 22636416HCID 22636416, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22636403HCID 22636403, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-2,3,5,8-tetrahydro-pyrazolo[1,2-a]pyridazin-1-one, 11, (2.4 g, 6.8 mmol) in THF:MeOH (80 mL of 1:1 mixture) is added dropwise a solution of OXONE® (16.8 g, 27.2 mmol) in H2O (80 mL). After stirring 2 hours at room temp, the reaction mixture is diluted with aqueous saturated NaHCO3 and extracted with EtOAc (3×). The combined organic phases are dried, filtered, and concentrated in vacuo to afford 1.5 g (58% yield) of the desired product as a yellow solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. customThe combined organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2b0247c9db4810a26b4befb29b4571
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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