Sodium Azide → 6-Azido-4-(quinolin-6-yloxy)-pyrimidine

HRID 2264566Notes

Reaction equation

HRID 2264566 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:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:19]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1)=[N+:20]=[N-:21]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 576000846-(6-Chloropyrimidin-4-yloxy)quinoline

Product 1

HCID 862346386-Azido-4-(quinolin-6-yloxy)-pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.4 g (36.4 mMol) of 6-chloro-4-(quinolin-6-yloxy)-pyrimidine in 110 ml DMF, 4.74 g (73 mMol) NaN3 are added. After stirring for 60 min at 60° C., the solution is diluted with EtOAc and water. The aqueous layer is separated off and extracted 2× with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrate in vacuo to give the crude title compound which is used as such in the next step: MS: [M+1]+=265.

Workup

  1. customThe aqueous layer is separated off
  2. extractionextracted 2× with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-09cd8d930764423eb407ad7bcf53dc3d
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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