4-Chloro-6-(4-nitrophenoxy)pyrimidine → 4-((6-Chloropyrimidin-4-yl)oxy)aniline

HRID 1993504Notes

Reaction equation

HRID 1993504 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1>CO.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 226137114-((6-Chloropyrimidin-4-yl)oxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-Chloro-6(4-nitro-phenoxy)-pyrimidine (Stage 21.2; 3.6 g, 14.3 mmol) dissolved in MeOH (250 ml) is hydrogenated in the presence of Raney-Ni (3 g) at 40° C. for 3 d. The reaction solution is filtered, concentrated under reduced pressure and crystallized from AcOEt/hexane to give the title compound of Stage 21.1: M+H=222/224; 1H-NMR (400 MHz, DMSO-d6): 8.62 (s, 1H), 7.13 (s, 1H), 6.83 (d, 9 Hz, 2H, phenyl), 6.56 (d, 9 Hz, 2H, phenyl), 5.12 (s, 2H, NH2); m.p.=135.5-138.1° C.

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated under reduced pressure
  3. customcrystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-72541af66510462990fe541834187f67
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…