Acetonitrile → 5-(Methylthio)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

HRID 40910

Reaktionsgleichung

Reaktionsgleichung von HRID 40910
[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.[CH3:23][S:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[C:29]#[N:30].C1CCN2C(=NCCC2)CC1.C(#N)C>>[CH3:23][S:24][CH2:25][CH2:26][CH:27]([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)[CH2:28][C:29]#[N:30]

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 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)-pyrimidineHCID 86613006(2E)-5-(methylthio)pent-2-enenitrile

Produkt 1

HCID 574776485-(Methylthio)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrileAusbeute 83,2 %

Versuchsvorschrift

A mixture of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (0.30 g, 0.00095 mol), (2E)-5-(methylthio)pent-2-enenitrile (0.28 g, 0.0016 mol) and DBU (45 0.00030 mol) in ACN (3 mL, 0.06 mol) was stirred at rt for 5 days. The solvent was removed by rotary evaporation to give an orange oil. The crude oil was chromatographed with 30-70 ethyl acetate/hex, to give 0.35 g of a colorless oil (83% yield).

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation
  2. customto give an orange oil
  3. customThe crude oil was chromatographed with 30-70 ethyl acetate/hex

Quellen und Nachweise

ORD-Eintrag
ord-baa43bbe872345dcb7ae3ae6f83b84d7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

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