Sodium hydride → 7-({6-[4-(Trifluoromethyl)phenyl]pyrimidin-4-yl}oxy)quinoline

HRID 858984ノート

反応式

HRID 858984 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[OH:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[N:26]2)=[CH:21][CH:20]=1.[H-].[Na+]>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][CH:25]=[N:26]4)=[CH:21][CH:20]=3)[CH:7]=2)=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidineHCID 1354268667-Hydroxyquinoline

生成物 1

HCID 104290187-({6-[4-(Trifluoromethyl)phenyl]pyrimidin-4-yl}oxy)quinoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a 250-mL, round-bottomed flask containing 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (2.5 g, 9.7 mmol) and 7-hydroxyquinoline (2.0 g, 14 mmol, Acros) in DMF (30 mL), was added NaH (5.4 g, 14 mmol, 60% in mineral oil, Aldrich) at room temperature The solution was then stirred at room temperature for 4 h. After the solvent was removed in vacuum, EtOAc (100 mL) and water (50 mL) were added to the residue. The solid precipitate was filtered and the filtrate was poured into a separatory funnel. The organic layer was separated, combined with the previously isolated solid, concentrated in vacuum, and purified by silica gel chromatography (2:1 hexanes/EtOAc). The purified product was dissolved in acetone (30 mL) and MeOH (10 mL), and to the solution was added water (30 mL) in small portions. The precipitated solid was filtered, washed with water (5 mL), and dried under vacuum at 50° C. for 48 h to furnish the title compound as a white solid. Mp: 178–180° C. MS (ESI, pos. ion) m/z: 368 (M+1). Anal. Calcd for C20H12F3N3O: C, 65.40; H, 3.29; N, 11.44. Found: C, 65.42; H, 3.23; N, 11.43.

後処理

  1. customAfter the solvent was removed in vacuum, EtOAc (100 mL) and water (50 mL)
  2. additionwere added to the residue
  3. filtrationThe solid precipitate was filtered
  4. additionthe filtrate was poured into a separatory funnel
  5. customThe organic layer was separated
  6. concentrationconcentrated in vacuum
  7. custompurified by silica gel chromatography (2:1 hexanes/EtOAc)
  8. dissolutionThe purified product was dissolved in acetone (30 mL)
  9. additionMeOH (10 mL), and to the solution was added water (30 mL) in small portions
  10. filtrationThe precipitated solid was filtered
  11. washwashed with water (5 mL)
  12. customdried under vacuum at 50° C. for 48 h

出典と根拠

ORDレコード
ord-e65870c54fe14014b575b4854c1d4a67
出典データセット
uspto-grants-2006_12
特許番号
US07148221B2

反応ノート

読み込み中…