Methane, dichloromethoxy- → HCID 10178654, 화합물

HRID 2250996노트

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HRID 2250996 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[N:11]([C:16]1[CH:21]=[C:20]([NH:22][CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[N:19]=[C:18]([CH3:28])[N:17]=1)[CH2:10][CH2:9]2.[CH:29]([O:32]C)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[N:11]([C:16]1[C:21]([CH:29]=[O:32])=[C:20]([NH:22][CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[N:19]=[C:18]([CH3:28])[N:17]=1)[CH2:10][CH2:9]2

참가 물질

5

반응물 3

HCID 21004Methane, dichloromethoxy-2회HCID 6451240Aluminum(III) ChlorideHCID 10270183HCID 10270183, 화합물

생성물 1

HCID 10178654HCID 10178654, 화합물수율 30%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

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온도
20 °C

실험 절차

To a suspension of AlCl3 (736 mg, 5.44 mmol) in CHCl3 (5 mL) a solution of 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.46 g, 4 mmol) in CHCl3 was added at 0° C., followed by Cl2CHOMe (0.4 mL, 4.4 mmol). The reaction was stirred at 0° C. for 2 h and at 20° C. for 16 h. Then an additional amount of Cl2CHOMe was added (0.2 mL, 2.2 mmol) and the reaction was continued for 26 h. The mixture was poured into ice/water (50 mL) and after quenching it was basified with 1 N NaOH, extracted with EtOAc (2×100 mL each) and the combined organic extracts were washed with water, brine, dried over (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent to give the product 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-formyl-2-methylpyrimidine (470 mg, 30% yield).

후처리

  1. additionwas added at 0° C.
  2. waitthe reaction was continued for 26 h
  3. customafter quenching it
  4. extractionextracted with EtOAc (2×100 mL each)
  5. washthe combined organic extracts were washed with water, brine
  6. dry with materialdried over (MgSO4)
  7. customThe residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent

출처 및 근거

ORD 기록
ord-bec63cb3b8484250accd055ec51bca10
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319100B2

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