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

HRID 965688ノート

反応式

HRID 965688 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cf1c2a6b1ce24e68a882b918e6e612c6
出典データセット
uspto-grants-2005_10
特許番号
US06951864B2

反応ノート

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