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Acetonitrile → Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate

HRID 40892
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 40892
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.[C:23]([OH:28])(=[O:27])[CH:24]=[CH:25][CH3:26].[CH2:29]1CCN2C(=NCCC2)C[CH2:30]1.[C:40](#N)C>>[CH3:26][C:25]([N:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1)([CH3:40])[CH2:24][C:23]([O:28][CH2:29][CH3:30])=[O:27]
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Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 194992-Butenoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 426313464-(1H-Pyrazol-4-yl)-7-(2-(trimethylsilyl)ethoxy)methyl-7 H-pyrrolo(2,3-d)-pyrimidine

Produkt 1

HCID 66597630Ethyl 3-methyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]butanoate
Ausbeute 91 %

Versuchsvorschrift

A solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (12.1 g, 0.0384 mol), 2-butenoic acid, 3-methyl-, ethyl ester (16.0 mL, 0.115 mol) and DBU (14.3 mL, 0.0959 mol) in ACN (100 mL) was heated at reflux for 3.5 hours. The solvent was removed in vacuo. The residue was diluted with water, extracted with ethyl acetate, and the combined organic extracts were washed with saturated ammonium chloride, dried over sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography (ethyl acetate/hexanes) to yield the desired product (15.5 g, 91%).

Aufarbeitung

  1. temperatureat reflux for 3.5 hours
  2. customThe solvent was removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washthe combined organic extracts were washed with saturated ammonium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7972b7e291a041bf8970498f74b98750
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530485B2

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