6-Azido-4-(quinolin-6-yloxy)-pyrimidine → 6-Amino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine

HRID 2264567Notes

Reaction equation

HRID 2264567 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:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:5]=1)=[N+]=[N-]>C1COCC1.C(O)(=O)C.[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:18](=[CH:19][CH:20]=2)[NH:17][CH2:16][CH2:15][CH2:14]3)[CH:5]=1

Participants

4

Reactant 1

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

Product 1

HCID 595964216-Amino-4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

The crude 6-azido-4-(quinolin-6-yloxy)-pyrimidine (36.4 mMol) in 324 ml of THF/acetic acid 4:1 is hydrogenated in the presence of 6 g Pd/C (10% Engelhard 4505). Then the catalyst is filtered off and the filtrate concentrated in vacuuo. The residue is put to pH 10 by addition of sat. Na2CO3 solution and extracted 3× with EtOAC. The organic phases are washed with water and brine, dried (Na2SO4) and after addition of 40 g of SiO2 concentrate in vacuo. The resulting powder is put on top of a SiO2 chromatography column and the title compound eluated with EtOAc: MS: [M+1]+=243.

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationthe filtrate concentrated in vacuuo
  3. additionThe residue is put to pH 10 by addition of sat. Na2CO3 solution
  4. extractionextracted 3× with EtOAC
  5. washThe organic phases are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. additionafter addition of 40 g of SiO2
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1f287d657c3e4a6b98a85972e4481076
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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