5-(6-Azido-pyrimidin-4-yloxy)-1H-indole → 5-(6-Amino-pyrimidin-4-yloxy)-1H-indole

HRID 2264593

Reaction equation

HRID 2264593 reaction equation
[N:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:5]=1)=[N+]=[N-]>C1COCC1.[Pd]>[NH2:1][C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:5]=1

Participants

4

Reactant 1

HCID 862347045-(6-Azido-pyrimidin-4-yloxy)-1H-indole

Product 1

HCID 219492665-(6-Amino-pyrimidin-4-yloxy)-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

480 mg (1.9 mMol) 5-(6-azido-pyrimidin-4-yloxy)-1H-indole in 25 ml THF are hydrogenated in presence of 75 mg Pd/C 10%. Filtration, concentration of the filtrate and column chromatography (SiO2; EtOAc/hexane 3:1→EtOAc) gives the title compound: MS: [M+1]+=227; TLC(EtOAc): Rf=0.11

Workup

  1. filtrationFiltration, concentration of the filtrate and column chromatography (SiO2; EtOAc/hexane 3:1→EtOAc)

Sources & evidence

ORD record
ord-44e175bf19d54bdb949918e394102f7a
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Linked notes

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