Hydrazine → [5-Amino-4-(2,4-dichlorophenyl) pyrimidin-2-yl]{[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amine

HRID 31807Notes

Reaction equation

HRID 31807 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:15]([N:26]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:14][N:13]=2)[CH:5]=[CH:4][C:3]=1[N+:37]([O-:39])=[O:38].NN>C(O)C>[NH2:26][C:15]1[C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[N:17][C:12]([NH:11][CH2:10][CH2:9][NH:8][C:6]2[CH:5]=[CH:4][C:3]([N+:37]([O-:39])=[O:38])=[C:2]([NH2:1])[N:7]=2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 221428712-[2-({2-[(6-Amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]isoindoline-1,3-dione

Product 1

HCID 22142459[5-Amino-4-(2,4-dichlorophenyl) pyrimidin-2-yl]{[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 mmol of 2-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)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-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino.

Workup

  1. custompurified by column chromatography
  2. washeluting with 5-10% methanol/methylene chloride
  3. customto obtain [5-amino-4-(2,4-dichlorophenyl)pyrimidin-2-yl]{2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino

Sources & evidence

ORD record
ord-57a6dc2115d74882a5fb44ac361c9b3c
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

Loading…