Réaction #4780

ord-7f820da542c94a05a709cf0743a91157

Équation de réaction

Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)Br
5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine
CN1CCNCC1
N-methylpiperazine
Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1C(C)N1CCN(C)CC1
6-methyl-5-[1-(4-methylpiperazin-1-yl)ethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine
Rendement 32.4%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewas refluxed for 1.5 hours
  2. 2
    AutreThe reaction mixture was evaporated in vacuo
  3. 3
    AutreThe residue was chromatographed on allumina
  4. 4
    workup.ADDITIONeluting with a mixture of ethyl acetate and n-hexane (1:20)
  5. 5
    workup.ADDITIONThe fractions containing the desired product
  6. 6
    Concentrationconcentrated in vacuo
  7. 7
    AutreThe residue was crystallized from a mixture of n-hexane and diethyl ether

Mode opératoire

A mixture of 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g) and N-methylpiperazine (1.13 g) in isopropylalcohol (15 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on allumina eluting with a mixture of ethyl acetate and n-hexane (1:20). The fractions containing the desired product were combined and concentrated in vacuo. The residue was crystallized from a mixture of n-hexane and diethyl ether to give 6-methyl-5-[1-(4-methylpiperazin-1-yl)ethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine (0.51 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04727073uspto-grants-1988_02