Tributyltin Chloride → 4-(3-Methyl-4-trifluoromethyl-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine

HRID 1927974ノート

反応式

HRID 1927974 の反応式
I[C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([CH3:27])[CH:18]=3)[N:8]=2)[CH:6]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:35]([Sn:39](Cl)([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH3:38].[Cl-].[NH4+]>C1COCC1>[CH3:27][C:19]1[CH:18]=[C:17]([C:9]2[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=[C:7]([N:5]3[CH:6]=[C:2]([Sn:39]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:35][CH2:36][CH2:37][CH3:38])[N:3]=[CH:4]3)[N:8]=2)[CH:22]=[CH:21][C:20]=1[C:23]([F:26])([F:25])[F:24]

参加物

6

反応物 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 574687872-(4-Iodo-imidazol-1-yl)-4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidineHCID 178461733HCID 178461733、化合物

生成物 1

HCID 574688314-(3-Methyl-4-trifluoromethyl-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-(4-iodo-imidazol-1-yl)-6-(3-methyl-4-trifluoromethyl-phenyl)-4-trifluoromethyl-pyrimidine (Example E.73) (1.49 g, 3.0 mmol) in THF (21 mL) was added at 0° C. isopropyl-magnesium chloride lithium chloride (1M in THF, 3.6 mL, 3.6 mmol). The reaction mixture was allowed to stir for 15 min at 0° C., tributyltin chloride (1.27 g, 3.9 mmol) was added, the reaction mixture was stirred at room temperature for 16 h, poured into saturated ammonium chloride solution (70 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (70 mL), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on alox (ethylacetate/heptane) to yield the title compound (0.33 g, 17%) as a light brown oil. MS (ISP) 663.3 [(M+H)+].

後処理

  1. customwas added at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 16 h
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with brine (70 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by flash chromatography on alox (ethylacetate/heptane)

出典と根拠

ORDレコード
ord-98734abe77c945caa85803314233a898
出典データセット
uspto-grants-2012_05
特許番号
US08183262B2

反応ノート

読み込み中…