Potassium Carbonate → 2-Fluoro-6-(1h-imidazol-2-yl)pyridine

HRID 916637Notes

Reaction equation

HRID 916637 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:12])=[N:6][CH:7]=[N:8][C:9]=1[CH2:10]Br)[CH2:2][CH3:3].C(C1C(Cl)=NC=NC=1CCl)CC.[F:25][C:26]1[N:31]=[C:30]([C:32]2[NH:33][CH:34]=[CH:35][N:36]=2)[CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:25][C:26]1[N:31]=[C:30]([C:32]2[NH:36][CH:35]=[CH:34][N:33]=2)[CH:29]=[CH:28][CH:27]=1.[Cl:12][C:5]1[N:6]=[CH:7][N:8]=[C:9]([CH2:10][N:36]2[CH:35]=[CH:34][N:33]=[C:32]2[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([F:25])[N:31]=2)[C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidineHCID 534265344-Chloro-6-(chloromethyl)-5-propylpyrimidine

Product 2

HCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223131636-Chloro-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Fluoro-2-(1H-imidazol-2-yl)-pyridine is prepared as described in Example 16 of U.S. patent application Ser. No. 10/038,069, filed Dec. 12, 2001 and published as US 2003/0069257 on Apr. 10, 2003, which is hereby incorporated by reference at page 31 for its teaching regarding the synthesis of this compound. A mixture of 102 or 5-propyl-6-chloromethyl-4-chloro-pyrimidine (1 mmol of either), 6-fluoro-2-(1H-imidazol-2-yl)-pyridine (163 mg, 1 mmol) and K2CO3 (552 mg, 4 mmol) in DMF (6 ml) is stirred at room temperature overnight. The solvent is removed in vacuo and EtOAc (10 ml) and water (10 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (10 ml), dried (Na2SO4) and evaporated. PTLC separation of the residue with 5% MeOH in CH2Cl2 provides the product (103) as a white solid.

Workup

  1. customthe synthesis of this compound
  2. customThe solvent is removed in vacuo and EtOAc (10 ml) and water (10 ml)
  3. additionare added to the residue
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  6. washThe combined extracts are washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customPTLC separation of the residue with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-c179f48f91c74431a810dec803063dad
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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