Morpholine → 4-(5-Bromopyrimidin-2-yl)morpholine

HRID 734347Notes

Reaction equation

HRID 734347 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C>[Br:14][C:11]1[CH:10]=[N:9][C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 51443624-(5-Bromopyrimidin-2-yl)morpholineYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.34 g) was added to a solution of 2-chloro-5-bromo-pyrimidine (0.5 g) in DMF (20 ml). The reaction mixture was stirred at rt for 15 min. Morpholine (0.2 g) was added and the reaction mixture was stirred at rt for 2 h. The excess DMF was removed by evaporation and the residue was partitioned between H2O/EtOAc (30:30 ml) The EtOAc layer was dried (MgSO4) and evaporated to dryness to give the sub-title compound as a cream solid (0.2 g). LCMS electrospray(+ve) 246 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at rt for 2 h
  2. customThe excess DMF was removed by evaporation
  3. customthe residue was partitioned between H2O/EtOAc (30:30 ml) The EtOAc layer
  4. dry with materialwas dried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ab2a6236d2154eccafc76ab11566ee69
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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