m-Chloroperbenzoic acid → HCID 136023973, compound

HRID 54948Notes

Reaction equation

HRID 54948 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:12]3[NH:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)=[C:12]3[NH:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[CH:7][CH:8]=1)=[O:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136470754HCID 136470754, compound

Product 1

HCID 136023973HCID 136023973, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-methylthiophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (190 mg) in dichloromethane (6 ml) was added m-chloroperbenzoic acid (127 mg) under ice cooling. The mixture was stirred at ambient temperature for 30 minutes and diluted with dichloromethane. The solution was washed with an aqueous saturated sodium thiosulfate solution, an aqueous saturated sodium bicarbonate solution and brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained crude solid was recrystallized from a mixture of 2-propanol and ether to give 2-(4-methylsulfinylphenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (168 mg).

Workup

  1. washThe solution was washed with an aqueous saturated sodium thiosulfate solution
  2. dry with materialan aqueous saturated sodium bicarbonate solution and brine, dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel
  5. customthe obtained crude solid
  6. customwas recrystallized from a mixture of 2-propanol and ether

Sources & evidence

ORD record
ord-5d8a97570afc40c996f768a4d15f384e
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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