Hydrogen Peroxide → HCID 21101370, compound

HRID 2375489Notes

Reaction equation

HRID 2375489 reaction equation
OO.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:14]=[C:13]([N:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:25][CH2:24]3)[N:12]=2)=[CH:6][CH:5]=1.C([O-])(O)=[O:36].[Na+]>C(Cl)Cl>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:14]=[C:13]([N:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N+:30]=4[O-:36])[CH2:27][CH2:28]3)[N:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 21101376HCID 21101376, compound

Product 1

HCID 21101370HCID 21101370, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-cholorperbenzoic acid (450 mg, 2.6 mmol), and 30% H2O2 (0.1 mL) in CH2Cl2 (2 mL) was added to a solution of N-(4-methylphenyl)-6-(1-piperidinyl)-2-[4-(2-pyridinyl)-1-piperazinyl]-4-pyrimidinamine (150 mg, 0.300 mmol) in CH2Cl2 at 0° C. The resulting mixture was gradually warmed to room temperature and stirred for 24 h, crude product was treated with saturated NaHCO3 (50 mL) and extracted with EtOAC (3×50 mL). Combined organic layers were washed with brine (2×50 mL), dried over Na2SO4, filtered, concentrated in vacuo, and purified by chromatography on silica using hexane/EtOAc (1:3) to give the desired product.

Workup

  1. extractionextracted with EtOAC (3×50 mL)
  2. washCombined organic layers were washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-c9511a8d3a1848b9a1db968d6383817d
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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