Réaction #1269846

ord-7ee3b7afe7fa4dbd882c8ceceaa0f2c8

Équation de réaction

CN1C(=O)c2c[nH]cc2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one
ClCc1ccc(-c2ccccn2)cc1
2-(4-(chloromethyl)phenyl)pyridine
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
CN1C(=O)c2cn(Cc3ccc(-c4ccccn4)cc3)cc2N2C1=N[C@@H]1CCC[C@@H]12
pure product
Rendement 16.9%
CN1C(=O)c2cn(Cc3ccc(-c4ccccn4)cc3)cc2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-((4-Pyridin-2yl)-benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one
Rendement 16.9%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe mixture is filtered through a 0.2 μL microfilter
  2. 2
    AutreThe filtrate is purified by a semi-preparative HPLC

Mode opératoire

A suspension of (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one (140 mg, 0.61 mmol), 2-(4-(chloromethyl)phenyl)pyridine (0.12 g, 0.61 mmol) and cesium carbonate (400 mg, 1.22 mmol) in anhydrous DMF is stirred at room temperature overnight. The mixture is filtered through a 0.2 μL microfilter. The filtrate is purified by a semi-preparative HPLC to give 41 mg of pure product as off white solids. MS (ESI) m/z 398.2 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08664207B2uspto-grants-2014_03