Ethanol → 5-(Methylthio)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]pentanenitrile

HRID 40911

Reaktionsgleichung

Reaktionsgleichung von HRID 40911
[CH3:1][S:2][CH2:3][CH2:4][CH:5]([N:9]1[CH:13]=[C:12]([C:14]2[C:15]3[CH:22]=[CH:21][N:20](COCC[Si](C)(C)C)[C:16]=3[N:17]=[CH:18][N:19]=2)[CH:11]=[N:10]1)[CH2:6][C:7]#[N:8].C1COCC1.C(O)C.[OH-].[NH4+]>Cl.O>[CH3:1][S:2][CH2:3][CH2:4][CH:5]([N:9]1[CH:13]=[C:12]([C:14]2[C:15]3[CH:22]=[CH:21][NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH:11]=[N:10]1)[CH2:6][C:7]#[N:8]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 574776485-(Methylthio)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

Produkt 1

HCID 177549055-(Methylthio)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]pentanenitrileAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 5-(methylthio)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile (0.35 g, 0.00079 mol) in THF (4 mL, 0.05 mol) and 3.0 M HCl (HCl) in water (4 mL) was heated to reflux overnight. The solvent was removed by rotary evaporation to give a pale orange oil. The oil was stirred in ethanol (3 mL, 0.05 mol) and 8.0 M ammonium hydroxide in water (1 mL) overnight. The reaction was concentrated and purified by prep LCMS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to give 125 mg of a white foam. The white foam was triturated with MTBE (˜1.5 mL). The resulting solid was filtered, washed and dried to give 80 mg of the product (32% yield).

Aufarbeitung

  1. temperatureto reflux overnight
  2. customThe solvent was removed by rotary evaporation
  3. customto give a pale orange oil
  4. concentrationThe reaction was concentrated
  5. custompurified by prep LCMS (C18 column
  6. washeluting with a gradient of ACN/H2O containing 0.15% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-b546328957a94d06bc5ca5c665024045
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

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