4-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine → 4-(2-(4-Aminophenoxy)phenyl)pyrimidin-2-amine

HRID 593987Notes

Reaction equation

HRID 593987 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[N:16]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 667316394-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 577562704-(2-(4-Aminophenoxy)phenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine (0.280 g, 0.908 mmol) and palladium, 10 wt. % (dry basis) on activated carbon 50% water wet (0.193 g, 0.182 mmol) were combined under nitrogen and diluted with 5 mL MeOH. The atmosphere was replaced with hydrogen, and the mixture was stirred rapidly overnight. The reaction was flushed with nitrogen and was filtered through celite, rinsing with MeOH. Concentration in vacuo afforded 4-(2-(4-aminophenoxy)phenyl)pyrimidin-2-amine MS m/z=279 [M+H]+. Calc'd for C16H14N4O: 278.3.

Workup

  1. customThe reaction was flushed with nitrogen
  2. filtrationwas filtered through celite
  3. washrinsing with MeOH
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-21aba716641b4cc28981b969f09a9ecd
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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