Water → HCID 67203989, compound

HRID 1615381Notes

Reaction equation

HRID 1615381 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.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:33][NH2:34].O>CS(C)=O>[CH3:33][NH:34][C:2]1[CH:3]=[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)[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 86672901HCID 86672901, compound

Product 1

HCID 67203989HCID 67203989, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

1-(6-Chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (200 mg, 0.57 mmol) and potassium carbonate (788 mg, 7.5 mmol) were dissolved in DMSO (5 mL). Methylamine hydrochloride (192 mg, 2.85 mmol) was added at room temperature. The reaction mixture was stirred at 100° C. for 15 hours. After cooling to room temperature, water was added and the reaction mixture was stirred for 1 hour. Thus prepared solid was filtered, washed with water, and dried in the air. N-Methyl-6-(6-(3-nitrophenyl)-1H-indol-1-yl)pyrimidin-4-amine (193 mg) was yielded as white solid.

Workup

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

Sources & evidence

ORD record
ord-87241b5d49224fedbc1fcd86ad3b6f98
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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