Cesium carbonate → HCID 86667380, compound

HRID 334170Notes

Reaction equation

HRID 334170 reaction equation
Br[CH2:2][C:3]([NH:5][CH:6]([C:8]1[NH:9][C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:13]=[C:12]([Cl:23])[N:11]=2)[CH3:7])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:23][C:12]1[N:13]=[C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:15]2[N:16]=[C:8]3[N:9]([C:10]=2[N:11]=1)[CH2:2][C:3](=[O:4])[NH:5][CH:6]3[CH3:7]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 178465002HCID 178465002, compound

Product 1

HCID 86667380HCID 86667380, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-N-[1-(2-chloro-6-morpholin-4-yl-9H-purin-8-yl)-ethyl]-acetamide (275 mg, 0.68 mmol) and cesium carbonate (0.48 g, 1.36 mmol) in anhydrous DMF (10 mL) was stirred at RT for 2 h, then diluted with water and extracted five times with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2) gradient 0-5% methanol in DCM) to give 3-Chloro-8-methyl-1-morpholin-4-yl-7,8-dihydro-2,4,4b,7,9-pentaaza-fluoren-6-one (93 mg, 42%). LCMS RT=2.41 min, [M+H]+=323/325

Workup

  1. extractionextracted five times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04a26b7759354514b6c2cbaa34a3f44c
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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