Ammonia → HCID 67204634, compound

HRID 1615376Notes

Reaction equation

HRID 1615376 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=4)[CH:15]=3)[CH:10]=[CH:9]2)[CH:3]=1.[NH3:26].C(O)(C)C.O>CS(C)=O>[N+:23]([C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][N:8]3[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:26])[CH:3]=3)=[CH:12][CH:13]=2)[CH:22]=[CH:21][CH:20]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 3776IsopropanolHCID 86672901HCID 86672901, compound

Product 1

HCID 67204634HCID 67204634, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

1-(6-Chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (1 g, 2.86 mmol) was dissolved in DMSO (15 mL) in a sealed reactor. After adding 2.0 M ammonia solution in isopropanol (15 mL, 30 mmol), the reaction mixture was stirred at 100° C. for 15 hours. After cooling to room temperature and adding water (70 mL), the reaction mixture was stirred at room temperature for 1 hour. Thus prepared solid was filtered, washed with water, and dried in the air. 6-(6-(3-Nitrophenyl)-1H-indol-1-yl)pyrimidin-4-amine (850 mg) was yielded as white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. filtrationThus prepared solid was filtered
  4. washwashed with water
  5. customdried in the air

Sources & evidence

ORD record
ord-5a36e45feac846988a4712f90cc61687
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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