N-[2-Amino-6-chloro-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine → N4-[3-Fluoro-4-(1H-indazol-5-yloxy)phenyl]pyrimidine-2,4-diamine

HRID 16466Notes

Reaction equation

HRID 16466 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[CH:19]4)=[C:11]([F:25])[CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1>C(O)C.[Pd]>[F:25][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[CH:19]2

Participants

4

Reactant 1

HCID 17979350N-[2-Amino-6-chloro-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine

Product 1

HCID 58733398N4-[3-Fluoro-4-(1H-indazol-5-yloxy)phenyl]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

50 mg (0.135 mmol) of 6-chloro-N4-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]pyrimidine-2,4-diamine (from example 8) are dissolved in ethanol. 50 mg of 10% palladium-on-carbon are added, and the suspension is stirred overnight under an atmosphere of hydrogen. The palladium catalyst is filtered off with suction and the filtrate is concentrated.

Workup

  1. filtrationThe palladium catalyst is filtered off with suction
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-f282461f438f4e4dba764611784a4da3
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…