HCID 67204634, compound → HCID 67203782, compound

HRID 1615377Notes

Reaction equation

HRID 1615377 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[C:19]3[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.O1CCOCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[C:19]3[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 67204634HCID 67204634, compound

Product 1

HCID 67203782HCID 67203782, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21966525Dioxane MethanolSolvent

Procedure

6-(6-(3-Nitrophenyl)-1H-indol-1-yl)pyrimidin-4-amine (400 mg, 1.21 mmol) was dissolved in methanol/dioxane (1:1, 6 mL) and Raney nickel was added. The mixture solution was stirred under hydrogen gas (1 atm) for 1.5 hours. The mixture solution was filtered through a diatomite pad, and the filtrate was concentrated under reduced pressure. After adding methylene chloride to the residue, thus prepared solid was filtered. 6-(6-(3-Aminophenyl)-1H-indol-1-yl)pyrimidin-4-amine (158 mg) was yielded as white solid. Concentration of the filtrate followed by column chromatography (silica gel, EA:Hx=1:1→MC:MeOH=20:1) further gave the target compound.

Workup

  1. filtrationThe mixture solution was filtered through a diatomite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionAfter adding methylene chloride to the residue, thus prepared solid
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-9600e79f36af4e2084490827c5e735d9
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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