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Triethylamine → 6-[2-(Tert-butyldimethylsilanyloxy)ethyl]-5,7-dichloropyrazolo[1,5-a]pyrimidine

HRID 1452617
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HRID 1452617 반응식
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.C(N(CC)CC)C.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23].[Cl-].[NH4+]>C(Cl)Cl>[Si:26]([O:10][CH2:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]2[N:5]([N:12]=[CH:13][CH:14]=2)[C:6]=1[Cl:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 575268292-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanol

생성물 1

HCID 575268026-[2-(Tert-butyldimethylsilanyloxy)ethyl]-5,7-dichloropyrazolo[1,5-a]pyrimidine수율 108.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a methylene chloride (50 mL) solution containing 2-(5,7-dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanol (640 mg, 2.77 mmol), triethylamine (3.86 mL, 27.7 mmol) and tert-butylchlorodimethylsilane (1.25 g, 8.31 mmol) were added, and this mixture was stirred at room temperature for 16 hr. After the reaction, aqueous ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off and the residue was purified with column chromatography (15% ethyl acetate-hexane) to obtain the title compound (1.04 g).

후처리

  1. additionwere added
  2. additionwas added to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialbrine and dried over sodium sulfate
  6. filtrationAfter the sodium sulfate was filtered off
  7. distillationthe solvent was distilled off
  8. customthe residue was purified with column chromatography (15% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-c289cf2202194a61afb7ccb7bf8e320c
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473694B2

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