Dichloromethane methanol → [6-(4-Amino-phenoxy)-pyrimidin-4-yl]-(4-methoxy-phenyl)-amine

HRID 1993507Notes

Reaction equation

HRID 1993507 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[N:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.CO.C(Cl)Cl>C1COCC1.CCO.[Ni]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:14]2[N:13]=[CH:12][N:11]=[C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:15]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 68535688(4-Methoxy-phenyl)-[6-(4-nitro-phenoxy)-pyrimidin-4-yl]-amine

Product 1

HCID 68540837[6-(4-Amino-phenoxy)-pyrimidin-4-yl]-(4-methoxy-phenyl)-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

(4-Methoxy-phenyl)-[6-(4-nitro-phenoxy)-pyrimidin-4-yl]-amine (Stage 47.2; 1.06 g, 3.13 mmol) dissolved in THF/EtOH (1:2; 27 mL) is hydrogenated in the presence of Raney-Ni (0.2 g) during 36 h. After filtering off the catalyst and washing with EtOH (20 mL), the solvent is evaporated under reduced pressure and flash chromatographed (silica gel, 4.5×26 cm, MeOH/CH2Cl2=5:95) giving a white solid: M+H=309.1; 1H-NMR (400 MHz, DMSO-d6): 9.23 (s, 1H, NH-pyrimidinyl), 8.22 (s, 1H, pyrimidine), 7.40/6.85/6.79/6.57 (d/d/d/d, 9.0 Hz, 8H, phenyl-oxo/phenyl-OMe), 5.81 (s, 1H, pyrimidinyl), 5.07 (s, 2H, NH2), 3.72 (s, 3H, CH3—O); Rf (MeOH/CH2Cl2=1:9): 0.44; HPLC (System 1): 3.45 min.

Workup

  1. filtrationAfter filtering off the catalyst
  2. washwashing with EtOH (20 mL)
  3. customthe solvent is evaporated under reduced pressure and flash
  4. customchromatographed (silica gel, 4.5×26 cm, MeOH/CH2Cl2=5:95)
  5. customgiving a white solid
  6. custom3.45 min.

Sources & evidence

ORD record
ord-8a97665921fb4d599da91b8ba703770f
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…