Hydrazine → [5-Amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))-amino]ethyl}amine

HRID 1825481Notes

Reaction equation

HRID 1825481 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([N:15]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:13][N:12]=[C:11]([NH:26][CH2:27][CH2:28][NH:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][N:31]=2)[N:10]=1.NN>C(O)C>[NH2:15][C:14]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[N:10][C:11]([NH:26][CH2:27][CH2:28][NH:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][N:31]=2)=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 221428102-[4-(2,4-Dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}-amino)pyrimidin-5-yl]isoindoline-1,3-dione

Product 1

HCID 22142671[5-Amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))-amino]ethyl}amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 mmol of 2-[4-(2,4-dichlorophenyl)-2-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidin-5-yl]isoindoline-1,3-dione and 20 mmol of hydrazine were stirred in ethanol at 75° C. for two hours and then purified by column chromatography eluting with 5-10% methanol/methylene chloride to obtain [5-amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine.

Workup

  1. custompurified by column chromatography
  2. washeluting with 5-10% methanol/methylene chloride

Sources & evidence

ORD record
ord-444b95709b7746aa8660e576ef306b12
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

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