6-[2-(2-Morpholin-4-ylethylamino)pyrimidin-4-yl]-2-(2-trimethylsilanyl-ethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one → 4-(1H-Benzimidazol-2-yl)-6-[2-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]-2H-pyridazin-3-one

HRID 12289Notes

Reaction equation

HRID 12289 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[C:18]([C:31]4[N:35](COCC[Si](C)(C)C)[C:34]5[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=5[N:32]=4)[C:19](=[O:30])[N:20](COCC[Si](C)(C)C)[N:21]=3)[CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>ClCCl.FC(F)(F)C(O)=O>[NH:35]1[C:34]2[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=2[N:32]=[C:31]1[C:18]1[C:19](=[O:30])[NH:20][N:21]=[C:16]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:15]=2)[CH:17]=1

Participants

4

Reactant 1

HCID 686811726-[2-(2-Morpholin-4-ylethylamino)pyrimidin-4-yl]-2-(2-trimethylsilanyl-ethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Product 1

HCID 1359787734-(1H-Benzimidazol-2-yl)-6-[2-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

88 mg of 6-[2-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]-2-(2-trimethylsilanyl-ethoxymethyl)-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one are dissolved in 2 ml of a 1:1 mixture of dichloromethane and trifluoroacetic acid, and the mixture is stirred at room temperature for 2 hours. The volatile components are then distilled off, the residue is dissolved in 1 ml of methanol, and 1 ml of a two molar aqueous sodium hydroxide solution is added. The solution is stirred at room temperature for 12 hours and then put directly onto the preparative RP-HPLC (0-100% acetonitrile (+0.05% formic acid) in water (+0.05% formic acid)) to isolate the product.

Workup

  1. distillationThe volatile components are then distilled off
  2. dissolutionthe residue is dissolved in 1 ml of methanol
  3. addition1 ml of a two molar aqueous sodium hydroxide solution is added
  4. stirringThe solution is stirred at room temperature for 12 hours
  5. customto isolate the product

Sources & evidence

ORD record
ord-1ed32532581c41498e6c601434eb109f
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Reaction notes

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