m-Chloroperbenzoic acid → N-(3-nitro-phenyl)-4-(N-oxido-3-pyridyl)-2-pyrimidine-amine

HRID 440873

Reaction equation

HRID 440873 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[N+:19]([O-:31])[CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9860872(3-Nitro-phenyl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amine

Product 1

HCID 22405644N-(3-nitro-phenyl)-4-(N-oxido-3-pyridyl)-2-pyrimidine-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

200 mg (0.68 mmol) of N-(3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine are suspended in 5 ml of methylene chloride, and 225 mg (0.71 mmol) of 3-chloroperbenzoic acid are added. After 2 hours a further 10 ml of methylene chloride are added. The suspension is stirred for a further 20 hours at room temperature. Filtration and flash chromatography of the residue (methylene chloride:methanol:25% aqueous ammonia solution=90:10:1) yield N-(3-nitro-phenyl)-4-(N-oxido-3-pyridyl)-2-pyrimidine-amine; Rf =0.4 (methylene chloride:methanol:25% aqueous ammonia solution=90: 10:1), m.p. 252°-258°.

Workup

  1. filtrationFiltration and flash chromatography of the residue (methylene chloride:methanol:25% aqueous ammonia solution=90:10:1)

Sources & evidence

ORD record
ord-c3431567551c499387cdf45b4c7175ae
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Linked notes

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