Sodium Azide → 6-Azido-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

HRID 916638Notes

Reaction equation

HRID 916638 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[C:3]=1[CH2:21][CH2:22][CH3:23].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[C:3]=1[CH2:21][CH2:22][CH3:23])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 223131636-Chloro-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Product 1

HCID 223131686-Azido-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 103 (2.25 mmol) and NaN3 (731 mg, 11.25 mmol) in DMF (15 ml) is heated at 70° C. in a sealed tube overnight. The solvent is removed in vacuo and water (10 ml) and EtOAc (10 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (2×10 ml). The combined extracts are washed with brine (15 ml) and dried with Na2SO4. The solvent is removed in vacuo and the resulting yellow oil (104) is used in the next step without further purification.

Workup

  1. customThe solvent is removed in vacuo and water (10 ml) and EtOAc (10 ml)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (2×10 ml)
  5. washThe combined extracts are washed with brine (15 ml)
  6. dry with materialdried with Na2SO4
  7. customThe solvent is removed in vacuo
  8. customthe resulting yellow oil (104) is used in the next step without further purification

Sources & evidence

ORD record
ord-c180fc79222d413f9fdc97e62223fd66
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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