Pyrazole → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyrazol-1-yl-pyrimidine

HRID 965688Notes

Reaction equation

HRID 965688 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.Cl[C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[C:13]([CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[N:12]=[CH:11][N:10]=1>C1COCC1>[F:30][C:29]1[C:24]([C:20]2[N:19]([CH2:18][C:13]3[C:14]([CH2:15][CH2:16][CH3:17])=[C:9]([N:3]4[CH:7]=[CH:6][CH:5]=[N:4]4)[N:10]=[CH:11][N:12]=3)[CH:23]=[CH:22][N:21]=2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 100423524-Chloro-6-{[2-(3-fluoro-2-pyridinyl)-1H-imidazol-1-yl]methyl}-5-propylpyrimidine

Product 1

HCID 100672694-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyrazol-1-yl-pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (15 mg, 60% in mineral oil, 0.37 mmol) in anhydrous THF (4 mL), a solution of pyrazole (20 mg, 0.3 mmol) in THF (3 mL) is added dropwise. The mixture is stirred at room temperature for 20 minutes. To the mixture, a solution of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (100 mg, 0.3 mmol) in THF (3 mL) is added. The mixture is stirred at room temperature overnight. The solvent is removed in vacuo. The residue is dissolved in DCM, and the mixture is washed with brine, dried over (MgSO4), filtered, and the solvent is evaporated. The residue is purified by preparative TLC with 10% MeOH/DCM to give the title compound. 1H-NMR (CDCl3) δ: 0.95 (t, 3H), 1.55-1.61 (m, 2H), 3.11 (t, 2H), 5.94 (s, 2H), 6.46-6.47 (m, 1H), 7.16 (s, 1H), 7.22 (s, 1H), 7.34 (s, 1H), 7.51 (t, 1H), 7.77 (d, 1H), 8.26 (s, 1H), 8.45 (d, 1H), 8.71 (s, 1H).

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customThe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in DCM
  4. washthe mixture is washed with brine
  5. dry with materialdried over (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customThe residue is purified by preparative TLC with 10% MeOH/DCM

Sources & evidence

ORD record
ord-cf1c2a6b1ce24e68a882b918e6e612c6
Source dataset
uspto-grants-2005_10
Patent number
US06951864B2

Reaction notes

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