Hydrochloric Acid → 3-methyl-2-[2-(4-piperidin-1-ylmethyl-phenyl)ethoxy]-6-pyridin-4-yl-3H-pyrimidin-4-one dihydrochloride

HRID 1468794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468794
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=1.[N:16]1([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][OH:31])=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N12CCCN=C1CCCCC2.[ClH:43]>CN(C)C=O.C(OCC)(=O)C.O>[ClH:1].[ClH:43].[CH3:8][N:7]1[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[N:3]=[C:2]1[O:31][CH2:30][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:24][CH:25]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 671652542-(4-Piperidin-1-ylmethylphenyl)ethanol

Produkt 1

HCID 679775993-methyl-2-[2-(4-piperidin-1-ylmethyl-phenyl)ethoxy]-6-pyridin-4-yl-3H-pyrimidin-4-one dihydrochlorideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (500 mg, 2.26 mmol) and 2-(4-piperidin-1-ylmethyl-phenyl)ethanol (990 mg, 4.51 mmol) in N,N-dimethylformamide (15 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (347 mg, 2.26 mmol) at room temperature. The mixture was stirred at 100° C. for 4 hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=90/10 to 67/33) to afford a pale blue powder. This compound was dissolved into ethyl acetate (1.2 ml), and 4N-hydrogen chloride in ethyl acetate (1.2 ml, 4.8 mmol) was added at room temperature. The mixture was stirred for 30 minutes, then the solvent was removed under reduced pressure to afford 3-methyl-2-[2-(4-piperidin-1-ylmethyl-phenyl)ethoxy]-6-pyridin-4-yl-3H-pyrimidin-4-one dihydrochloride as a pale purple solid (455 mg, 0.952 mmol, 42%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=90/10 to 67/33)
  6. customto afford a pale blue powder
  7. additionwas added at room temperature
  8. stirringThe mixture was stirred for 30 minutes
  9. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-16ef100bf10a4ee786350d9638076881
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006232B2

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