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Diethyl Ether → 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 861144
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Reaktionsgleichung

Reaktionsgleichung von HRID 861144
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=3)[C:10]([C:11](=O)[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[CH:23]1([NH:28][C:29]([NH2:31])=[NH:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C)C=O.O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=3)[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:29]([NH:28][CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:30]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1
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Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 574447371-[7-Chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, Verbindung

Produkt 1

HCID 865967674-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (4.04 g, 13.0 mmol) in N,N-dimethylformamide (100 mL) was added cyclopentyl guanidine hydrochloride (6.36 g, 39 mmol), followed by solid potassium carbonate (5.39 g, 39 mmol). The resultant solution was heated to reflux for 6 hours. Upon cooling to room temperature, ether was added followed by water. The organics were washed with brine, and the aqueous extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (3:10 ethyl acetate:hexanes) to give 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (2.39 g, 43%) as a yellow foam. 1H NMR (CDCl3) δ 8.47 (d, 1H), 7.99 (d, 1H), 7.48 (s, 1H), 7.39 (d, 1H), 7.33–7.24 (m, 3H), 7.05 (d, 1H), 6.33 (d, 1H), 5.38 (broad s, 1H), 4.36 (m, 1H), 2.40 (s, 3H), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.58 (m, 2H); MS m/z 404 (M+1).

Aufarbeitung

  1. temperatureto reflux for 6 hours
  2. washThe organics were washed with brine
  3. extractionthe aqueous extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (3:10 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-485d09d83293425fade5f4235992ea36
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07153855B2

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