Dimethylformamide → 4-(3-Nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine

HRID 853265

Reaktionsgleichung

Reaktionsgleichung von HRID 853265
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[C:23]1[C:24]2[C:31]([CH3:32])=[C:30]([CH3:33])[NH:29][C:25]=2[N:26]=[CH:27][N:28]=1>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:23]1[C:24]2[C:31]([CH3:32])=[C:30]([CH3:33])[NH:29][C:25]=2[N:26]=[CH:27][N:28]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 130411444-chloro-5,6-dimethyl-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 589311454-(3-Nitrophenoxy)-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidineAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

After adding 3-nitrophenol (243 mg), potassium carbonate (268 mg) and dimethylformamide (2 ml) to the 4-chloro-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (177 mg) described in journal of Medicinal Chemistry, 1996, Vol. 39, No. 12, 2285–2292, the mixture was stirred at 120–130° C. for 72 hours. This was returned to room temperature, water was added, extraction was performed with a tetrahydrofuran and ethyl acetate mixed solution, and then the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to dryness. The obtained crystals were washed with diethyl ether to obtain the title compound (130 mg).

Aufarbeitung

  1. customThis was returned to room temperature
  2. extractionextraction
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. washThe obtained crystals were washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f0ce1a45be374457836e72b9b1a478cc
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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