Triethylamine → HCID 178420115, compound

HRID 1057309Notes

Reaction equation

HRID 1057309 reaction equation
[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:16][CH:17]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1.[OH-].[NH4+]>C(O)C>[C:1]1([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([N:18]4[CH2:23][CH2:22][N:21]([C:32]5[N:37]=[CH:36][CH:35]=[CH:34][N:33]=5)[CH2:20][CH2:19]4)=[N:16][CH:17]=3)[NH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 14923Ammonium HydroxideHCID 744042-Chloropyrimidine2×HCID 18671610HCID 18671610, compound

Product 1

HCID 178420115HCID 178420115, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Reference: J. Am. Chem. Soc. 1954, 1484) A solution of 1-[5-(5-phenyl-1H-imidazol-2-yl)-pyridin-2-yl]-piperazine (0.16 g, 0.52 mmol), triethylamine (0.22 ml, 0.16 g, 1.58 mmol, 3.0 equiv) and 2-chloro-pyrimidine (0.90 mg, 0.79 mmol, 1.5 equiv) in absolute ethanol (5 ml) under nitrogen atmosphere was heated at reflux for 1 hour, after which additional triethylamine (0.22 ml, 0.16 g, 1.58 mmol, 3.0 equiv) and 2-chloro-pyrimidine (0.90 mg, 0.79 mmol, 1.5 equiv) were added. The reaction was heated at reflux for an additional 1.5 hour, then stirred at room temperature for two days. The mixture was basified to pH 10 with concentrated ammonium hydroxide, and then concentrated in vacuo. The residue was partitioned between water (20 ml) and ethyl acetate (50 ml). The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a solid, which was triturated with ether to give the desired product (0.15 g, 74%). MS m/z 446 (M++1).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction was heated
  3. temperatureat reflux for an additional 1.5 hour
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between water (20 ml) and ethyl acetate (50 ml)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a solid, which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-3f53b134cbea49a8932477bc30116af0
Source dataset
uspto-grants-2003_02
Patent number
US06514966B2

Reaction notes

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