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

HRID 1487617

反応式

HRID 1487617 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-e32306cdd8734c56a51926d4908d835e
出典データセット
uspto-grants-2016_08
特許番号
US09428509B2

関連ノート

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