methyl-[9-(4-nitrophenyl)-9H-purin-6-yl]amine → [9-(4-aminophenyl)-9H-purin-6-yl]-methylamine

HRID 1912855Notes

Reaction equation

HRID 1912855 reaction equation
[CH3:1][NH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1.[H][H]>CO.[C].[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:7]2[CH:6]=[N:5][C:4]3[C:8]2=[N:9][CH:10]=[N:11][C:3]=3[NH:2][CH3:1])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 23155308methyl-[9-(4-nitrophenyl)-9H-purin-6-yl]amineHCID 178418361HCID 178418361, compound

Product 1

HCID 23155065[9-(4-aminophenyl)-9H-purin-6-yl]-methylamineYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 1,000 mL of methanol, 13.0 g (48 mmol) of methyl-[9-(4-nitrophenyl)-9H-purin-6-yl]amine was suspended, and 1.8 g of 10% palladium carbon was added thereto, and the suspension was stirred in a hydrogen atmosphere at 60° C. for six hours. The palladium carbon was removed by Celite filtration, and the product was concentrated under reduced pressure, and the obtained crude product was purified by a silica gel column (ethyl acetate:methanol=9.1) to obtain 8.2 g (70%) of a target product as a pale yellow solid.

Workup

  1. customThe palladium carbon was removed by Celite filtration
  2. concentrationthe product was concentrated under reduced pressure
  3. customthe obtained crude product
  4. customwas purified by a silica gel column (ethyl acetate:methanol=9.1)

Sources & evidence

ORD record
ord-4c235c2b64e14e6c85f69502298212df
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

Loading…