m-Chloroperbenzoic acid → 2-(4-fluorophenyl)-6-methoxy-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 7670

Reaction equation

HRID 7670 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[N:11]3[CH2:12][CH:13]([O:15][CH3:16])[CH2:14][N:10]3[C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=2)=[CH:4][CH:3]=1.Cl[C:28]1C=CC=C(C(OO)=O)C=1.[S:38](=[O:41])(O)[O-:39].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[N:11]3[CH2:12][CH:13]([O:15][CH3:16])[CH2:14][N:10]3[C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:38]([CH3:28])(=[O:41])=[O:39])[N:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 219921842-(4-fluorophenyl)-6-methoxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 207247422-(4-fluorophenyl)-6-methoxy-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Fluorophenyl)-6-methoxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 49, (1.10 g, 2.95 mmol) is diluted with dichloromethane (60 mL). 3-Chloroperbenzoic acid (662 mg of ˜77% purity, 2.95 mmol) is added all at once to the yellow suspension. After 20 min, additional 3-chloroperbenzoic acid (240 mg, 1.07 mmol) is added. After 10 minutes, the clear, yellow reaction solution is poured in a 10% aqueous solution of sodium bisulfite (60 mL). The layers are separated and the aqueous layer extracted with dichloromethane (2×50 mL). The combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (2×50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 948 mg of a mixture of the corresponding sulfoxide and sulfone as a yellow solid. Used as is for next step.

Workup

  1. waitAfter 10 minutes
  2. customThe layers are separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×50 mL)
  4. washThe combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9376f5d373fb4f039f78d34ca6b522f9
Source dataset
uspto-grants-2006_08
Patent number
US07087615B2

Linked notes

Loading…