2-Chloro-5-nitrobenzonitrile → 1,3-dimethyl-6-{4-[3-(2-cyano-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

HRID 1085277Notes

Reaction equation

HRID 1085277 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17](S(CC)(=O)=O)[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:32])[N:4]([CH3:33])[C:3]1=[O:34].ClC1C=CC([N+]([O-])=O)=CC=1[C:38]#[N:39]>CN(C)C=O>[CH3:1][N:2]1[C:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][C:23]=3[C:38]#[N:39])[CH2:12][CH2:13]2)=[CH:6][C:5](=[O:32])[N:4]([CH3:33])[C:3]1=[O:34]

Participants

4

Reactant 2

HCID 855042-Chloro-5-nitrobenzonitrileHCID 20061072HCID 20061072, compound

Product 1

HCID 200611961,3-dimethyl-6-{4-[3-(2-cyano-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedioneYield 154.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.3 g of Compound 158 obtained beforehand, 0.3 g of 2-chloro-5-nitrobenzonitrile and 0.31 ml of trtiethylamine were stirred at 80° C. for 1 hour in 5 ml of dimethylformamide. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=40/1, by volume), thereby obtaining 0.4 g of 1,3-dimethyl-6-{4-[3-(2-cyano-4-nitroanilino)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=40/1, by volume)

Sources & evidence

ORD record
ord-df36c8d6c9f04c058a8b35314c43a1ef
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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