Water → 4-ethoxy-5-iodo-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1396137노트

반응식

HRID 1396137 반응식
[CH2:1]([O:3][C:4]1[C:5]2[C:12]([I:13])=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2].[H-].[Na+].[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].O>O1CCCC1>[CH2:1]([O:3][C:4]1[C:5]2[C:12]([I:13])=[CH:11][N:10]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])[C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 584858444-ethoxy-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 584857284-ethoxy-5-iodo-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine수율 93.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 4-ethoxy-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (12, 2.70 g, 9.34 mmol) in 60.0 mL of tetrahydrofuran under an atmosphere of nitrogen, sodium hydride (411.0 mg, 10.27 mmol) is added. The reaction is stirred at room temperature for 20 minutes, then triisopropylsilyl chloride (3, 2.177 mL, 10.27 mmol) is added. The reaction is stirred at room temperature for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 5-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (13, 3.90 g).

후처리

  1. stirringThe reaction is stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with 5-100% ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-2c4063f5da554358bd05a351e02d3aff
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901118B2

반응 노트

불러오는 중…