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

HRID 1989251노트

반응식

HRID 1989251 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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 a lox (ethylacetate/heptane) to yield the title compound (0.33 g, 17%) as a light brown oil. MS (ISP) 663.3 [(M+H)+].

후처리

  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 a lox (ethylacetate/heptane)

출처 및 근거

ORD 기록
ord-972dc87bef4b43a0adfd616e46eb125a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642264B2

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