m-Chloroperbenzoic acid → HCID 69751029, compound

HRID 586420Notes

Reaction equation

HRID 586420 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[CH:21]=[C:20]([N:22]([CH3:24])[CH3:23])[N:19]=[C:18]([S:25][CH3:26])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[CH:21]=[C:20]([N:22]([CH3:23])[CH3:24])[N:19]=[C:18]([S:25]([CH3:26])=[O:35])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69750792HCID 69750792, compound

Product 1

HCID 69751029HCID 69751029, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N4-[3-(benzyloxy)phenyl]-N6,N6-dimethyl-2-(methylsulfanyl)-4,6-pyrimidinediamine (5.5 g, 15 mmol) and m-chloroperbenzoic acid (5.19 g) in CH2Cl2 at 0° C. was stirred for 1 hour. The reaction mixture was slowly brought to room temperature and quenched with a solution of sodium sulfite. The organic layer was separated and washed with NaHCO3 solution (3×250 mL), dried over anhydrous MgSO4, concentrated, and purified by column chromatography [eluent: chloroform/methanol (94:6)], giving N4-[3-(benzyloxy)phenyl]-N6,N6-dimethyl-2-(methylsulfinyl)-4,6-pyrimidinediamine (3.98, 69%).

Workup

  1. customwas slowly brought to room temperature
  2. customquenched with a solution of sodium sulfite
  3. customThe organic layer was separated
  4. washwashed with NaHCO3 solution (3×250 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. custompurified by column chromatography [eluent: chloroform/methanol (94:6)]

Sources & evidence

ORD record
ord-848780ff72fc443d912424cf46a56f62
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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