2-Chloro-5-nitropyridine → [4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-ol

HRID 1823531Notes

Reaction equation

HRID 1823531 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[C:18]([CH2:29][OH:30])=[CH:17][N:16]=1>CO.C(Cl)Cl>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:19]1[C:18]([CH2:29][OH:30])=[CH:17][N:16]=[C:15]([NH:14][CH2:13][CH2:12][NH:11][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[N:20]=1

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 22142936{2-[(2-Aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl]methan-1-ol

Product 1

HCID 22142375[4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-olYield 51%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The process of Example 140 is repeated using 2-chloro-5-nitro-pyridine and {2-[(2-aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl}methan-1-ol. Chromatography of the residue (silica gel, 5% methanol/methylene chloride) afforded 200 mg (51%) of [4-(2,4-dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]methan-1-ol as a yellow solid.

Sources & evidence

ORD record
ord-8368614a59fa4ca0878ca4f7d1ec7fb9
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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