m-Chloroperbenzoic acid → 7-Cyclohexyl-6-(4-methanesulfinyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 270951Notes

Reaction equation

HRID 270951 reaction equation
[CH:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[C:11]3[N:10]=[CH:9][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)(Cl)Cl>[CH:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[C:11]3[N:10]=[CH:9][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:26])=[O:32])=[CH:21][CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 159581417-Cyclohexyl-6-(4-methylsulfanylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 184458857-Cyclohexyl-6-(4-methanesulfinyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cloudy solution of 14 mg (0.038 mmol) of 7-cyclohexyl-6-(4-methylsulfanyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid in 2 mL of chloroform was added 9 mg (1.5 equiv) of m-chloroperoxybenzoic acid (mCPBA) and the cloudy solution became clear. Since after 5 min of stirring at rt TLC indicated disappearance of starting material, the mixture was concentrated to a residue which was purified via reverse-phase chromatography (using Gilson) to afford (after lyophilization) 10 mg (69% yield) of 7-cyclohexyl-6-(4-methanesulfinyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (491) as a solid as indicated by LC-MS—calcd for C20H21N3O3S [M++H]+: 384.13, found: 384.2.

Workup

  1. concentrationthe mixture was concentrated to a residue which
  2. customwas purified via reverse-phase chromatography (using Gilson)

Sources & evidence

ORD record
ord-a0802fd876224388bfb19ac1eb521379
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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