Tetrahydrofuran → HCID 59564353, compound

HRID 2096266Notes

Reaction equation

HRID 2096266 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[CH:24]=[N:25][C:26](SC)=[N:27][CH:28]=3)[CH2:13][CH2:12]2)=[O:10])[N:3]=1.O[O:32][S:33]([O-:35])=O.[K+].[CH2:37]1COCC1>O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[CH:24]=[N:25][C:26]([S:33]([CH3:37])(=[O:35])=[O:32])=[N:27][CH:28]=3)[CH2:13][CH2:12]2)=[O:10])[N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59564546HCID 59564546, compound

Product 1

HCID 59564353HCID 59564353, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2-(3,5-dimethyl-pyrazol-1-yl)-1-{4-[2-(2-methylsulfanyl-pyrimidin-5-yl)-phenyl]-piperazin-1-yl}-ethanone (210 mg, 0.497 mmol) in THF (5 mL) is added a solution of oxone (611 mg, 0.994 mmol) in water (5 mL). The mixture is allowed to stir at room temperature for 4 h. Water (10 mL) is added and the mixture is extracted with EtOAc 3×. The organic extracts are washed with water, brine, dried (Na2SO4) and concentrated. The residue is re-dissolved in dichloromethane (3 mL) and loaded on a 10 g Biotage SNAP column and eluted with 100% EtOAc to provide 2-(3,5-dimethyl-pyrazol-1-yl)-1-{4-[2-(2-methanesulfonyl-pyrimidin-5-yl)-phenyl]-piperazin-1-yl}-ethanone (102 mg).

Workup

  1. extractionthe mixture is extracted with EtOAc 3×
  2. washThe organic extracts are washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue is re-dissolved in dichloromethane (3 mL)
  6. washeluted with 100% EtOAc

Sources & evidence

ORD record
ord-8bdd9c50a9564f36a0ea36aa3a6050b4
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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