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 44926

Reaktionsgleichung

Reaktionsgleichung von HRID 44926
[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]

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]butanoateAusbeute 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-b11fff147ad14f93835b89a5ef7ad466
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541425B2

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