1-Bromo-2,4-dimethyl-5-nitrobenzene → 1-(2,2-Diethoxyethyl)-N-(2,4-dimethyl-5-nitrophenyl)-3-(pyrimidin-5-yl)-1H-pyrazole-5-amine

HRID 1055693Notes

Reaction equation

HRID 1055693 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[CH2:5][N:6]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)=[N:7]1)[CH3:2].Br[C:22]1[C:23]([CH3:32])=[CH:24][C:25]([CH3:31])=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1>>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]1[C:10]([NH:11][C:22]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([CH3:31])=[CH:24][C:23]=2[CH3:32])=[CH:9][C:8]([C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)=[N:7]1)[CH3:20]

Participants

3

Reactant 2

HCID 124743261-Bromo-2,4-dimethyl-5-nitrobenzeneHCID 897001301-(2,2-Diethoxyethyl)-3-(pyrimidin-5-yl)-1H-pyrazole-5-amine

Product 1

HCID 897001941-(2,2-Diethoxyethyl)-N-(2,4-dimethyl-5-nitrophenyl)-3-(pyrimidin-5-yl)-1H-pyrazole-5-amine

Procedure

Analogously to Example 13A/Step 1, 3.01 g (10.8 mmol) of the compound of Example 78A and 2.75 g (11.9 mmol) of 5-bromo-2,4-dimethylnitrobenzene gave, after 3 h of heating under reflux, a crude product which was purified by chromatography on a Biotage system (100 g Snap column; mobile phase gradient ethyl acetate/0-8% methanol). This gave 3.70 g (65% of theory) of the title compound.

Workup

  1. customgave, after 3 h
  2. temperatureof heating
  3. temperatureunder reflux
  4. customa crude product which was purified by chromatography on a Biotage system (100 g Snap column; mobile phase gradient ethyl acetate/0-8% methanol)

Sources & evidence

ORD record
ord-8131db893fa7490c807b234d04aab7fa
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

Loading…