m-Chloroperbenzoic acid → N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(N-oxido-4-pyridyl)-2-pyrimidine-amine

HRID 440877

Reaction equation

HRID 440877 reaction equation
[F:1][C:2]([F:26])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[F:26][C:2]([F:1])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N+:23]([O-:35])=[CH:22][CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9799152(4-Pyridin-4-yl-pyrimidin-2-yl)-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

Product 1

HCID 19966995N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(N-oxido-4-pyridyl)-2-pyrimidine-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.37 mmol)of N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(4-pyridyl)-2-pyrimidine-amine are suspended in 10 ml of methylene chloride and to the suspension are added 430 mg(1.37 mmol) of m-chloroperbenzoic acid and the reaction mixture is stirred for 4 hours at RT. After extraction with water and 2N sodium hydroxide solution, the organic phase is dried and concentrated on a rotovap. Chromatography (methylene chloride:methanol=19:1 to 9:1) and subsequent crystallisation (methylene chloride:diethyl ether) give N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(N-oxido-4-pyridyl)-2-pyrimidine-amine in the form of lemon yellow crystals; FAB-MS: 381 (M+ +H), m.p. 191°-192°.

Workup

  1. extractionAfter extraction with water and 2N sodium hydroxide solution
  2. customthe organic phase is dried
  3. concentrationconcentrated on a rotovap
  4. customChromatography (methylene chloride:methanol=19:1 to 9:1) and subsequent crystallisation (methylene chloride:diethyl ether)

Sources & evidence

ORD record
ord-8737f5feaab84da28d2f414d3cdff312
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Linked notes

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