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Potassium Carbonate → tert-Butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate

HRID 1626810
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1626810
Cl.[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:32]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:32]3[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][N:33]=3)[CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 67156013tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride

Produkt 1

HCID 58257552tert-Butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylateAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride (6.5 g, 15 mmol), 2,5-dibromopyridine (5.3 g, 7.5 mmol) and potassium carbonate (6.2 g, 45 mmol) were suspended in N,N-dimethylformamide (150 mL), followed by stirring at 100° C. for 22 hours. The reaction solution was concentrated under reduced pressure, followed by addition of ethyl acetate, and subsequently the organic layer was washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.3 g, 4.1 mmol) as a colorless oil (yield 27%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionfollowed by addition of ethyl acetate
  3. washsubsequently the organic layer was washed with water
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.40 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1646245145b04f69b739554e3183614c
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785462B2

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