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Diisopropylethylamine → 2-{4-[4-(2-tert-Butyl-6-trifluoromethyl-pyrimidin-4-yl)-piperazin-1-yl]butyl}-2H-[1,2,4]triazine-3,5-dione hydrochloride

HRID 453647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453647
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[CH:8]=[N:7]1.[C:14]([C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[C:20]([C:30]([F:33])([F:32])[F:31])[N:19]=1)([CH3:17])([CH3:16])[CH3:15].[Br-].[Na+].C(N(CC)C(C)C)(C)C>CN(C)C=O>[ClH:1].[C:14]([C:18]1[N:23]=[C:22]([N:24]2[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:11](=[O:12])[NH:10][C:9](=[O:13])[CH:8]=[N:7]3)[CH2:28][CH2:29]2)[CH:21]=[C:20]([C:30]([F:31])([F:32])[F:33])[N:19]=1)([CH3:17])([CH3:15])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 253881Sodium BromideHCID 158171752-(4-Chloro-butyl)-2H-[1,2,4]triazine-3,5-dioneHCID 183996102-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidine

Produkt 1

HCID 675122702-{4-[4-(2-tert-Butyl-6-trifluoromethyl-pyrimidin-4-yl)-piperazin-1-yl]butyl}-2H-[1,2,4]triazine-3,5-dione hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

13.4 g of 2-(4-chloro-butyl)-2H-[1,2,4]triazine-3,5-dione (65.8 mmol) and 18.97 g of 2-tert-butyl-4-piperazin-1-yl-6-trifluoromethyl-pyrimidine (65.8 mmol) were dissolved in 400 mL of dimethylformamide. After addition of 33.9 g of sodium bromide (329 mmol) and 115 mL of N,N-diisopropylethylamine (658 mmol), the reaction was stirred for 48 h at room temperature. Then the solvent was removed under reduced pressure and the obtained residue was trituated with 400 mL of ethyl acetate and the obtained solution was filtered. The filtrate was evaporated to dryness and the remaining oily residue was treated with 100 mL of diethyl ether, filtered and the filtrate was again evaporated to dryness. The crude product was purified three times via silica gel chromatography (ethyl acetate-methanol 0-100%; dichloromethane-methanol 0-5%; dichloro-methane-methanol 0-2%) to yield the free base of the title compound. This product was transferred into its hydrochloride salt via treatment with HCl/diethyl ether (yield 2.56 g).

Aufarbeitung

  1. customThen the solvent was removed under reduced pressure
  2. filtrationthe obtained solution was filtered
  3. customThe filtrate was evaporated to dryness
  4. additionthe remaining oily residue was treated with 100 mL of diethyl ether
  5. filtrationfiltered
  6. customthe filtrate was again evaporated to dryness
  7. customThe crude product was purified three times via silica gel chromatography (ethyl acetate-methanol 0-100%; dichloromethane-methanol 0-5%; dichloro-methane-methanol 0-2%)

Quellen und Nachweise

ORD-Eintrag
ord-653ba22409ef4710a04fb53f33b90b3e
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492540B2

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