(3-Nitro-phenyl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amine → N-(3-aminophenyl)-4-(3-pyridyl)-2-pyrimidine-amine

HRID 440867

Reaction equation

HRID 440867 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 9860872(3-Nitro-phenyl)-(4-pyridin-3-yl-pyrimidin-2-yl)-amine

Product 1

HCID 9943194N-(3-aminophenyl)-4-(3-pyridyl)-2-pyrimidine-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 17.0 g (0.058 mol) of N-(3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine in 1700 ml of tetrahydrofuran is stirred with 1.7 g of palladium on active carbon (5%) under a hydrogen atmosphere at normal pressure for 21 hours. The suspension is filtered and the filtrate is concentrated in a rotary evaporator. The yellow solid product that remains behind is stirred overnight in 200 ml of methylene chloride. Filtration and drying yield N-(3-aminophenyl)-4-(3-pyridyl)-2-pyrimidine-amine; m.p. 89°-90°, Rf =0.38 (chloroform:methanol=9:1).

Workup

  1. filtrationThe suspension is filtered
  2. concentrationthe filtrate is concentrated in a rotary evaporator
  3. filtrationFiltration
  4. customdrying

Sources & evidence

ORD record
ord-f9a9443399c54090be49c210593fd829
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Linked notes

Loading…