Diisopropylethylamine → 2-[1-(6-Chloro-5-methoxy-2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridine

HRID 1169806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169806
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[N:5]=[C:4]([CH3:11])[N:3]=1.C(N(C(C)C)CC)(C)C.[NH:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[CH2:23][CH2:22]1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CC(N(C)C)=O>[Cl:10][C:6]1[N:5]=[C:4]([CH3:11])[N:3]=[C:2]([N:21]2[CH2:22][CH2:23][CH:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[N:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[CH2:25][CH2:26]2)[C:7]=1[O:8][CH3:9]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 582936514,6-dichloro-5-methoxy-2-methylPyrimidineHCID 666409192-(Piperidin-4-YL)-1,8-naphthyridine

Produkt 1

HCID 866189262-[1-(6-Chloro-5-methoxy-2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridineAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

30 ml of dimethylacetamide, 0.9 g (4.66 mmoles) 4,6-dichloro-2-methyl -5-methoxy-pyrimidine and 3 ml of diisopropylethylamine are added into a single-necked flask containing 1.1 g (5.2 mmoles) of 2-piperidin-4-yl-[1,8]naphthyridine. This mixture is heated at 120° C. for 4 hours then concentrated to dryness under reduced pressure (2 kPa). The residue obtained is taken up in a mixture of water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The collected organic phases are dried over magnesium sulphate then the solvent is evaporated off under reduced pressure (2 kPa). The residue is chromatographed on silica gel eluting with a gradient of heptane-ethyl acetate of 100-0 to 0-100. 870 mg of expected product is obtained in the form of a yellow solid.

Aufarbeitung

  1. concentrationthen concentrated to dryness under reduced pressure (2 kPa)
  2. customThe residue obtained
  3. customThe organic phase is separated
  4. dry with materialThe collected organic phases are dried over magnesium sulphate
  5. customthe solvent is evaporated off under reduced pressure (2 kPa)
  6. customThe residue is chromatographed on silica gel eluting with a gradient of heptane-ethyl acetate of 100-0 to 0-100

Quellen und Nachweise

ORD-Eintrag
ord-b9e3fe95e4574baaa445431f2438cd94
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825119B2

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