Dimethylformamide → 4-(4,6-Dichloropyrimidin-2-yl)morpholine

HRID 889832Notes

Reaction equation

HRID 889832 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[NH2:19][C:20]1[N:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[N:21]=1>C(OCC)(=O)C>[Cl:27][C:22]1[CH:23]=[C:24]([Cl:26])[N:25]=[C:20]([N:19]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 27720684-(4,6-Dichloropyrimidin-2-yl)morpholineYield 28.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-bromoethylether (3.65 g), potassium carbonate (8.29 g), and N,N-dimethylformamide (75 mL) were added to 2-amino-4,6-dichloropyrimidine (2.46 g), and the mixture was refluxed for 3 hours while heated. Subsequently, the reaction mixture was diluted with ethyl acetate, was washed with water, and was dried over anhydrous sodium sulfate. The solvent was removed and the resulting residue was purified on a silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 4,6-dichloro-2-(morpholine-4-yl)pyrimidine (985 mg, 28%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperaturewhile heated
  3. washwas washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe resulting residue was purified on a silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-c84c5764f47a416d967f79e473225a06
Source dataset
uspto-grants-2006_02
Patent number
US06995153B2

Reaction notes

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