Potassium Carbonate → HCID 69224391, Verbindung

HRID 971192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971192
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][NH:19][CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:22].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[CH2:21][CH2:20][N:19]([C:23]4[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 59021490N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 69224391HCID 69224391, VerbindungAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of N-(4-tert-butylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine 0.173 g, 0.61 mmol), 2,3-dichloropyridine (0.91 g, 0.61 mmol) and potassium carbonate (0.234 g, 1.84 mmol) in DMF was heated in a sealed tube in a microwave oven (Emrys Optimizer model, Personal Chemistry) at 200° C. for 2 h. The mixture was cooled to r.t. and diluted with water (30 mL). The mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to leave an oil. The product was purified by silica gel chromatography (ethyl acetate/hexane gradient) to obtain 0.035 g of the title compound as a light yellow oil. The oil was dissolved in 1 mL ethyl acetate and treated with 1.0 M HCl in diethyl ether (0.09 mL). The resulting solid was collected by filtration, washed with diethyl ether and dried to give 0.030 g light yellow solid.

Aufarbeitung

  1. temperatureThe mixture was cooled to r.t.
  2. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto leave an oil
  7. customThe product was purified by silica gel chromatography (ethyl acetate/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-ed4e5b9d80764f2db55ad5c9c65fdf9a
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312330B2

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