Water → methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1766172

Reaktionsgleichung

Reaktionsgleichung von HRID 1766172
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.Cl[C:15]1[C:16]2[CH:23]=[CH:22][N:21]([CH3:24])[C:17]=2[N:18]=[CH:19][N:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[CH3:24][N:21]1[C:17]2[N:18]=[CH:19][N:20]=[C:15]([N:1]3[C:5]4=[N:6][CH:7]=[CH:8][CH:9]=[C:4]4[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]3)[C:16]=2[CH:23]=[CH:22]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Produkt 1

HCID 21110083methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylateAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 1.9 g (9.2 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 50 cm3 of dimethylsulfoxyde under argon atmosphere, were added 1.85 g (11.0 mmol) of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, followed by 3.2 g (23.0 mmol) of potassium carbonate. The reaction mixture was heated at about 120° C. for 24 hours, upon which it was cooled to about 20° C. and treated with 200 cm3 of distilled water. The mixture was then treated with 300 cm3 and 150 cm3 of ethyl acetate and filtered on Celite®. The aqueous phase was extracted with 150 cm3 of ethyl acetate. The combined organic extracts were dried on magnesium sulfate and concentrated to dryness in vacuo (2.7 kPa). The residue was purified via column chromatography on silica gel (0,04–0,06 mm), with dichloromethane/methanol 99:1 v/v as eluting solvent. Thus, 1.25 g of methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were obtained as a light-yellow crystalline powder. mp: 207° C.

Aufarbeitung

  1. temperaturewas cooled to about 20° C.
  2. filtrationfiltered on Celite®
  3. extractionThe aqueous phase was extracted with 150 cm3 of ethyl acetate
  4. customThe combined organic extracts were dried on magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo (2.7 kPa)
  6. customThe residue was purified via column chromatography on silica gel (0,04–0,06 mm), with dichloromethane/methanol 99:1 v/v
  7. washas eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-f419793e4f1b472aad89c56087eeb7fa
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230007B2

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