m-Chloroperbenzoic acid → HCID 20825605, compound

HRID 586422Notes

Reaction equation

HRID 586422 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:19][CH2:18]2)[N:4]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>OO.C([O-])(O)=O.[Na+]>[CH3:33][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:6]=[C:5]([N:17]2[CH2:18][CH2:19][N:20]([C:23]3[C:28]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:26]=[CH:25][N+:24]=3[O-:42])[CH2:21][CH2:22]2)[N:4]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10161497HCID 10161497, compound

Product 1

HCID 20825605HCID 20825605, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N4,N4-dimethyl-N6-(4-methylphenyl)-2-{4-[3-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl}-4,6-pyrimidinediamine (150, mg, 0.33 mmol), m-chloroperbenzoic acid (56 mg, 0.33 mmol) and 30% H2O2 (2 drops) were stirred at 0° C. for 24 hours. The crude product was then treated with saturated NaHCO3 solution (2×100 mL). The organic layer was separated, dried over MgSO4, concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (eluent: EtOAc), giving the desired product (12 mg, 8%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin-layer chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-7a3a135eb51843e3b01f9e1c9da7b7ca
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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