Cesium carbonate → HCID 46209435, compound

HRID 1182664Notes

Reaction equation

HRID 1182664 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][NH:10][CH:11]=[C:5]2[N:4]2[C@H:12]3[CH2:17][CH2:16][CH2:15][C@H:13]3[N:14]=[C:3]12.Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:24][CH:25]=3)[CH:11]=[C:5]2[N:4]2[C@H:12]3[CH2:17][CH2:16][CH2:15][C@H:13]3[N:14]=[C:3]12

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 219897292-(4-(Chloromethyl)phenyl)pyridineHCID 67378655HCID 67378655, compound

Product 1

HCID 46209435HCID 46209435, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-7ee3b7afe7fa4dbd882c8ceceaa0f2c8
Source dataset
uspto-grants-2014_03
Patent number
US08664207B2

Reaction notes

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