Ethanol → 4-(1H-Benzimidazol-2-yl)-6-(2-cyclopropylpyrimidin-4-yl)-2H-pyridazin-3-one

HRID 12297Notes

Reaction equation

HRID 12297 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[CH:11]=[C:12]([C:25]4[N:29](COCC[Si](C)(C)C)[C:28]5[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=5[N:26]=4)[C:13](=[O:24])[N:14](COCC[Si](C)(C)C)[N:15]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.C(O)C>Cl.O1CCOCC1>[NH:29]1[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[N:26]=[C:25]1[C:12]1[C:13](=[O:24])[NH:14][N:15]=[C:10]([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:9]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 686798776-(2-Cyclopropylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Product 1

HCID 1359787914-(1H-Benzimidazol-2-yl)-6-(2-cyclopropylpyrimidin-4-yl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

27 mg of 6-(2-cyclopropylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one are dissolved in 2.5 ml of 4M hydrochloric acid solution in dioxane and 1 ml of ethanol and stirred at room temperature for 2 days. The solvent is then distilled off, and the residue is dissolved in 2 ml of dichloromethane and 1 ml of trifluoroacetic acid and again stirred at room temperature for 3 h. Distillation off is then repeated, and the residue is dissolved in 1 ml of 2M sodium hydroxide solution and 2 ml of water, and the mixture is stirred at room temperature for 10 h. For workup, it is neutralized with 2M hydrochloric acid, the volatile components are distilled off, and the crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH)).

Workup

  1. distillationThe solvent is then distilled off
  2. dissolutionthe residue is dissolved in 2 ml of dichloromethane
  3. distillationDistillation
  4. dissolutionthe residue is dissolved in 1 ml of 2M sodium hydroxide solution
  5. stirring2 ml of water, and the mixture is stirred at room temperature for 10 h
  6. distillationthe volatile components are distilled off
  7. customthe crude product is purified by RP HPLC (acetonitrile (+0.05% HCOOH)/water (+0.05% HCOOH))

Sources & evidence

ORD record
ord-836e08e052fe43058a58ca664df681f1
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Reaction notes

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