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

HRID 2264592

Reaction equation

HRID 2264592 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:3]=1)=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 574551565-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

490 mg (2.0 mMol) 5-(6-chloro-pyrimidin-4-yloxy)-indole (WO 03/099771; Stage 163.1) and 260 mg (4.0 mMol) NaN3 in 3 ml DMF are stirred for 3 h at 90° C. Then the reaction mixture is poured into water and extracted three times with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated, yielding the title compound: MS: [M+1]+=253.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe organic layers are washed twice with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-15e27e7259fb44428da90c0ce67e12f8
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Linked notes

Loading…