Potassium cyanate → N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]urea

HRID 915956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915956
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.[O-:27][C:28]#[N:29].[K+]>O>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:28]([NH2:29])=[O:27])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

4

Edukt 2

HCID 11378442Potassium cyanateHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Produkt 1

HCID 136005909N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]ureaAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a 2 ml water/4 ml acetic acid solution of 200 mg (0.567 mmol) of the compound obtained in Example 44, 377 mg (4.65 mmol) of potassium cyanate was added, and the mixture was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to obtain 126 mg (56%) of the captioned compound.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-adcd3048f48247309f78177bec219178
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268128B2

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