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

HRID 911172Notes

Reaction equation

HRID 911172 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-25f70afaeab44fa88f0e3b0a9beaa425
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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