Sodium hydride → 4-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol

HRID 529677

반응식

HRID 529677 반응식
[H-].[Na+].[CH3:3][C:4]1([OH:11])[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1.[Cl:12][C:13]1[N:14]=[C:15](Cl)[C:16]2[C:21]([I:22])=[CH:20][N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=2[N:18]=1>C1COCC1>[Cl:12][C:13]1[N:14]=[C:15]([O:10][CH:7]2[CH2:8][CH2:9][C:4]([CH3:3])([OH:11])[CH2:5][CH2:6]2)[C:16]2[C:21]([I:22])=[CH:20][N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=2[N:18]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 144496821-Methylcyclohexane-1,4-diolHCID 866796212,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

생성물 1

HCID 867264454-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of sodium hydride (60% in mineral oil, 1.36 equiv) in dry THF (0.68 M) under nitrogen atmosphere was added 1-methylcyclohexane-1,4-diol (1 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 (0.9 equiv,) in dry THF (0.45 M) was added. The mixture was stirred at room temperature for 2 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 (20 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-30% ethyl acetate in petroleum ether) to afford the title compound as a white solid (78% yield). MS (ESI) m/z 538.4 [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 (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel flash column chromatography (0-30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-98948115e8ac471c89ed73a7be48b2a1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346812B2

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