Morpholine → 5-(4-Chlorophenylethynyl)-2-diisopropylaminomethyleneamino-4-morpholinopyrimidine

HRID 1271035Notes

Reaction equation

HRID 1271035 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:17]=[CH:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[N:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(#N)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]#[C:8][C:7]2[C:2]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[N:3][C:4]([N:17]=[CH:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[N:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 734464494-Chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

Product 1

HCID 685655885-(4-Chlorophenylethynyl)-2-diisopropylaminomethyleneamino-4-morpholinopyrimidineYield 120.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.46 g of 4-chloro-2-diisopropylaminomethyleneamino-5-(4-chlorophenylethynyl)-pyrimidine, 40 mL of acetonitrile and 0.41 g of morpholine was stirred at room temperature for 18 hours. The mixture was evaporated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was washed once more with water, dried over sodium sulfate and filtered. The filtrate was loaded on a column of silica gel equilibrated in the same solvent. After elution of an unknown impurity, the product eluted as a yellow band. Additional material was obtained by a final elution with 1:1 dichloromethane and ethyl acetate. Like fractions of the two eluants were pooled and evaporated to give 0.63 g of a yellow oil, 5-(4-Chlorophenylethynyl)-2-diisopropylaminomethyleneamino-4-morpholinopyrimidine.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue partitioned between water and dichloromethane
  3. washThe organic layer was washed once more with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. washAfter elution of an unknown impurity
  7. washthe product eluted as a yellow band
  8. customAdditional material was obtained by a final
  9. washelution with 1:1 dichloromethane and ethyl acetate
  10. customevaporated

Sources & evidence

ORD record
ord-070f0f7f8fc9418ebc13f579a877e26b
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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