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

HRID 965688노트

반응식

HRID 965688 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cf1c2a6b1ce24e68a882b918e6e612c6
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951864B2

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