Morpholine → HCID 57592522, compound

HRID 1784387Notes

Reaction equation

HRID 1784387 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17](Cl)[N:16]=2)[CH:14]=1>CN(C=O)C>[Br:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24758Sodium hydrideHCID 57592519HCID 57592519, compound

Product 1

HCID 57592522HCID 57592522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of morpholine (0.256 g, 2.94 mmol) in anhydrouse DMF (5 ml) was added NaH (0.117 g, 2.94 mmol, 60% disp' in mineral oil). The mixture was stirred at this temperature for 30 minutes before the addition of 4-(4-Bromo-imidazol-1-yl)-2-chloro-pyrimidine (0.64 g, 2.45 mmol). The reaction vessel was sealed and heated under the infuenceof microwave radiation for 7 minutes (120° C., High absorption setting). Upon cooling the mixture was diluted with water (7 ml) and the resultant yellow precipitate removed by filtration and purified by flash chromatography (SiO2) (4:1—Hexanes:EtOAc) to give the title compound as a white solid in analytically (0.76 g, 38.6%) pure form. m/z (LC-MSW, ESP):310.3 [M+H]+, R/T=3.26 mins.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated under the infuenceof microwave radiation for 7 minutes
  3. custom(120° C., High absorption setting)
  4. temperatureUpon cooling the mixture
  5. additionwas diluted with water (7 ml)
  6. customthe resultant yellow precipitate removed by filtration
  7. custompurified by flash chromatography (SiO2) (4:1—Hexanes:EtOAc)

Sources & evidence

ORD record
ord-c0d2761665384129aebcdcaf6ef4867a
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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