Acetic Acid → HCID 53736740, compound

HRID 1872053Notes

Reaction equation

HRID 1872053 reaction equation
B.[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:32][CH3:33])[C:13]1[N:18]=[C:17]([C:19]([N:21]2[CH2:26][CH2:25][C:24]3([O:30][CH2:29][CH2:28][O:27]3)[CH2:23][CH2:22]2)=O)[CH:16]=[C:15]([CH3:31])[N:14]=1.C(O)(=O)C.C(OCC)(=O)C>C1COCC1>[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:32][CH3:33])[C:13]1[N:18]=[C:17]([CH2:19][N:21]2[CH2:22][CH2:23][C:24]3([O:30][CH2:29][CH2:28][O:27]3)[CH2:25][CH2:26]2)[CH:16]=[C:15]([CH3:31])[N:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6331BoraneHCID 8857Ethyl AcetateHCID 18689809HCID 18689809, compound

Product 1

HCID 53736740HCID 53736740, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (1M, 29 mL, 29 mmol) was added dropwise to a solution of N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(4,4-ethylenedioxy-piperidino)carbonyl-6-methylpyrimidinamine (1.67 g, 3.3 mmol) in anhydrous THF (7 mL) with stirring under a nitrogen atmosphere. The reaction mixture was heated to reflux temperature and stirred for 20 h, then cooled to ambient temperature. A solution of glacial acetic acid was added dropwise; then the reaction mixture was heated to reflux temperature and stirred for 4 h, then cooled to ambient temperature. The reaction mixture was concentrated in vacuo; the residue was treated with excess 1N NaOH solution, and extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give an oil. Column chromatography (ethyl acetate) afforded N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(4,4-ethylenedioxy-piperidino)methyl-6-methylpyrimidinamine as a pale brown oil (860 mg); CI-MS; 489, 491 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. stirringstirred for 20 h
  4. temperaturethen the reaction mixture was heated
  5. temperatureto reflux temperature
  6. stirringstirred for 4 h
  7. temperaturecooled to ambient temperature
  8. concentrationThe reaction mixture was concentrated in vacuo
  9. additionthe residue was treated with excess 1N NaOH solution
  10. extractionextracted three times with ethyl acetate
  11. dry with materialThe combined organic layers were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto give an oil

Sources & evidence

ORD record
ord-2d476795930a4feb9b9bfe6e8d729b58
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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