Potassium Carbonate → 4-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

HRID 965686Notes

Reaction equation

HRID 965686 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].[F:13][C:14]1[C:15]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[N:16][CH:17]=[CH:18][CH:19]=1.[C:25]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:9]([CH2:10][N:24]2[CH:23]=[CH:22][N:21]=[C:20]2[C:15]2[C:14]([F:13])=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=[C:7]([CH3:25])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidineHCID 223131643-Fluoro-2-(1H-imidazol-2-yl)pyridine

Product 1

HCID 99977004-Chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-methyl-5-propyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-propyl-6-bromomethyl-4-chloro-pyrimidine (1 mmol), 3-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. Preparative TLC separation of the residue with 5% MeOH in CH2Cl2 provides the title compound as a white solid. 1H-NMR (CDCl3) δ: 8.65 (S, 1H), 8.24 (d, 1H), 7.53 (t, 1H), 7.32 (s, 1H), 7.27-7.22 (m, 1H), 7.12 (s, 1H), 5.87 (s, 2H), 2.76 (t, 2H), 1.68-1.54 (m, 2H), 1.01 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-5a42393d343846b98da02358bcffce09
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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