Diisopropylethylamine → 1-{4-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]butyl}-5-methyl-1H-pyrimidine-2,4-dione

HRID 1640459

Reaktionsgleichung

Reaktionsgleichung von HRID 1640459
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14].[Cl:15][C:16]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[Br-].[Na+].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[Cl:15][C:16]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:17]=1[CH2:18][N:19]1[CH2:20][CH2:21][N:22]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]2=[O:14])[CH2:23][CH2:24]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 253881Sodium BromideHCID 4111791-(2,4-Dichlorobenzyl)piperazineHCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 117188101-{4-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]butyl}-5-methyl-1H-pyrimidine-2,4-dioneAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

1-(4-Chlorobutyl)-5-methyl-1H-pyrimidine-2,4-dione (0.69 mmol, 0.15 g), 1-(2,4-dichlorobenzyl)piperazine (0.62 mmol, 0.15 g), sodium bromide (3.46 mmol, 0.36 g) and diisopropylethylamine (6.92 mmol, 0.89 g) were heated in N-methylpyrrolidinone (0.6 ml) at 120° C. for 5 hours. The reaction mixture was then allowed to cool, the suspension was filtered with suction, and the filtrate was concentrated. The residue was then then taken up in ethyl acetate and washed with saturated brine. The organic layer was dried, filtered to remove the desiccant and evaporated in vacuo. The resulting residue was purified by chromatography on silica gel (eluent: methyl tert-butyl ether/methanol (0-100%), resulting in 88.0 mg of the title compound.

Aufarbeitung

  1. temperatureto cool
  2. filtrationthe suspension was filtered with suction
  3. concentrationthe filtrate was concentrated
  4. washwashed with saturated brine
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customto remove the desiccant and
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by chromatography on silica gel (eluent

Quellen und Nachweise

ORD-Eintrag
ord-85ba6cec0af0423ba4949588bab461f4
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114875B2

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