1-Phenylpiperazine → 5-(4-Phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine

HRID 2294032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294032
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br.Br.Br[CH2:23][C:24]1[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=1>O1CCCC1>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:23][C:24]3[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Produkt 1

HCID 214736725-(4-Phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamineAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.14 g (0.00086 mol) of 1-phenyl-piperazine in 10 ml of tetrahydrofuran was treated with 0.6 ml (0.0043 mol) of triethylamine and 0.24 g (0.00086 mol) of 5-bromomethyl-pyrimidine-2,4-diamine dihydrobromide and the mixture was stirred at room temperature under argon for 16 hours. The suspension obtained was suction filtered and the filtrate was completely freed from the solvents. The residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether. 0.14 g (57%) of 5-(4-phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine was obtained as white crystals; m.p. 263°-265°. A further 0.04 g of yellowish crystals was recovered from the mother liquor.

Aufarbeitung

  1. customThe suspension obtained
  2. filtrationfiltered
  3. customThe residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-be4176dd37174086b95cef00aec5ab70
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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