Ethyl Acetate → Acetic Acid 2-{4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-pyrimidin-5-yl}-ethyl ester

HRID 916658Notes

Reaction equation

HRID 916658 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])=[C:7]([Cl:15])[N:6]=[CH:5][N:4]=1.[F:16][C:17]1[C:18]([C:23]2[NH:24][CH:25]=[CH:26][N:27]=2)=[N:19][CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Cl:15][C:7]1[C:8]([CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])=[C:3]([CH2:2][N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[C:18]2[C:17]([F:16])=[CH:22][CH:21]=[CH:20][N:19]=2)[N:4]=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 223131643-Fluoro-2-(1H-imidazol-2-yl)pyridineHCID 57503307Acetic Acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl ester

Product 1

HCID 57503309Acetic Acid 2-{4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-pyrimidin-5-yl}-ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 162 (8.4 mmol), 3-fluoro-2-(1H-imidazol-2-yl)-pyridine (described above) (1.38 g, 8.4 mmol) and K2CO3 (1.17 g, 8.4 mmol) in DMF (6 ml) is stirred at room temperature overnight. To the mixture are added EtOAc (20 ml) and water (10 ml). The organic layer is separated and the aqueous layer is extracted with EtOAc (3×10 ml). The combined extracts are washed with brine (10 ml), dried (Na2SO4) and solvent evaporated. PTLC separation of the residue (5% MeOH in CH2Cl2) gives the product (163) as a white solid.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with EtOAc (3×10 ml)
  3. washThe combined extracts are washed with brine (10 ml)
  4. dry with materialdried (Na2SO4) and solvent
  5. customevaporated
  6. customPTLC separation of the residue (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3ae0893890ae449489ee12669ddcd425
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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