Water → 5-(4-Iodo-pyridin-2-yloxy)-pyrimidine

HRID 40568

Reaction equation

HRID 40568 reaction equation
[N:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[N:3][CH:2]=1.[H-].[Na+].F[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][N:12]=1.O>CN(C=O)C>[I:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([O:7][C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 565855Pyrimidin-5-olHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 666349945-(4-Iodo-pyridin-2-yloxy)-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 259 mg (26.9 mmol) pyrimidin-5-ol (J. Chem. Soc. 1956, 2033) in 200 mL DMF are added 108 mg (26.9 mmol) sodium hydride (60% dispersion in mineral oil). The mixture is stirred for 20 min at r.t. After that time, 500 mg (22.4 mmol) 2-fluoro-4-iodopyridine are added and the mixture is stirred for 12 h at 80° C. Subsequently the mixture is poured into water and extracted with ethyl acetate (3×). The combined organic layers are washed with brine. After drying over sodium sulphate, the solvent is removed in vacuo and the residue is purified by column chromatography (silica gel; heptane/EtOAc, 100/0→40/60).

Workup

  1. stirringthe mixture is stirred for 12 h at 80° C
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialAfter drying over sodium sulphate
  5. customthe solvent is removed in vacuo
  6. customthe residue is purified by column chromatography (silica gel; heptane/EtOAc, 100/0→40/60)

Sources & evidence

ORD record
ord-758d3432bd7e4951ae9ed34d7b515c70
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Linked notes

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