Isopropanol → HCID 86726464, 화합물

HRID 529692노트

반응식

HRID 529692 반응식
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].[Cl:7][C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1>C1COCC1>[Cl:7][C:8]1[N:9]=[C:10]([O:6][CH:4]([CH3:5])[CH3:3])[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 866796212,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

생성물 1

HCID 86726464HCID 86726464, 화합물수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of sodium hydride (1 equiv, 60% in mineral oil) in dry THF (0.9 M) under nitrogen atmosphere was added propan-2-ol (0.52 equiv). The reaction mixture was stirred at room temperature for 30 min before a solution of 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (0.5 equiv) in dry THF (0.45 M) was added. The mixture was stirred at room temperature for 1 h. The reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether) to afford the title compound as a yellow oil (81% yield). MS (ESI) m/z 468.2 [M+1]+.

후처리

  1. additionwas added
  2. customUpon completion, the reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-ef922f1edf504f1d90ce9afbedb5e03d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346812B2

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