1,2-Dibromoethane → HCID 86667385, compound

HRID 334173Notes

Reaction equation

HRID 334173 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:11]([NH:13][CH3:14])[CH3:12])[NH:8]2)=[C:4]([N:15]2[CH2:20]CO[CH2:17][CH2:16]2)[N:3]=1.[C:21](=[O:24])([O-])[O-].[Cs+].[Cs+].Br[CH2:28][CH2:29]Br>CN(C=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:21][O:24][CH2:17][CH2:16]2)[C:5]2[N:6]=[C:7]3[N:8]([C:9]=2[N:10]=1)[CH2:29][CH2:28][N:13]([CH3:14])[CH:11]3[CH3:12]

Participants

6

Reactant 3

HCID 78391,2-Dibromoethane2×HCID 10796Cesium carbonateHCID 178483312HCID 178483312, compound

Product 1

HCID 86667385HCID 86667385, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of: [1-(2-chloro-6-morpholin-4-yl-9H-purin-8-yl)-ethyl]-methyl-amine (95 mg, 0.32 mmol), cesium carbonate (652 mg, 2 mmol) and 1,2-dibromoethane (0.030 mL, 0.35 mmol) in DMF (5 mL) was stirred at RT for 4 h. Another portion of 1,2-dibromoethane (0.030 mL, 0.35 mmol) was added and stirring was continued for 20 h. The reaction mixture was diluted with water and extracted seven times with ether. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2) gradient 0-4% methanol in DCM) to give 3-Chloro-7,8-dimethyl-1-morpholin-4-yl-5,6,7,8-tetrahydro-2,4,4b,7,9-pentaaza-fluorene (76 mg, 74%). LCMS RT=1.82 min, [M+H]+=323/325

Workup

  1. stirringstirring
  2. waitwas continued for 20 h
  3. extractionextracted seven times with ether
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1a1a0e123294f18bfab00f375bd95b8
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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