Water → HCID 58315460, Verbindung

HRID 1962196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962196
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:20]([CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].O.[C:30](=O)(O)[O-].[Na+]>C1COCC1.C[Mg]I>[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:20]([CH:21]2[CH2:26][CH2:25][C:24]([OH:27])([CH3:30])[CH2:23][CH2:22]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 67239800N,N-Dimethyl-7-(4-oxocyclohexyl)-2-(2-pyridinylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Produkt 1

HCID 58315460HCID 58315460, VerbindungAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418373HCID 178418373, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-(4-oxo-cyclohexyl)-2-(pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (25 mg, 0.066 mmol) in THF is added 20 drops of MeMgI. After reaction is completed, added 25 mL of water then 30 mL of aqueous sodium bicarbonate. Extraction with dichloromethane (3×50 mL) and concentrated to give a mixture of diastereomers. Preparative HPLC to give 7-(4-hydroxy-4-methyl-cyclohexyl)-2-(pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (2 mg, 4%). MS(ESI) m/z 395.3 (M+H)+

Aufarbeitung

  1. customAfter reaction
  2. extractionExtraction with dichloromethane (3×50 mL)
  3. concentrationconcentrated
  4. customto give
  5. additiona mixture of diastereomers

Quellen und Nachweise

ORD-Eintrag
ord-d42b9e74672043b6b5961a73f009af6d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415355B2

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