Triethylamine → HCID 67250567, compound

HRID 2421003Notes

Reaction equation

HRID 2421003 reaction equation
O[CH2:2][C:3]1[O:7][C:6]([C:8]2[C:9]([O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[N:10][C:11]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[N:12][CH:13]=2)=[N:5][N:4]=1.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C.C(=O)([O-])O.[Na+].[CH3:51][N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>ClCCl>[CH3:51][N:52]1[CH2:57][CH2:56][N:55]([CH2:2][C:3]2[O:7][C:6]([C:8]3[C:9]([O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])=[N:10][C:11]([NH:14][CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[N:12][CH:13]=3)=[N:5][N:4]=2)[CH2:54][CH2:53]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 67249772HCID 67249772, compound

Product 1

HCID 67250567HCID 67250567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 20 mL of dichloromethane, 5-(5-hydroxymethyl[1,3,4]oxadiazol-2-yl)-2-[2-(4-pyridyl)ethylamino]-4-(2-trimethylsilylethoxy)pyrimidine (0.76 g, 1.83 mmol) obtained in Step 2 was dissolved, then methanesulfonic anhydride (0.48 g, 2.75 mmol) and triethylamine (0.37 g, 3.66 mmol) were added thereto, followed by stirring at room temperature for 1 hour. After completion of the reaction was confirmed by thin-layer chromatography, saturated aqueous sodium hydrogen carbonate solution was added and the reaction mixture was separated. Further, an aqueous layer was extracted with dichloromethane and those organic layers were combined. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (50 mL), then 1-methylpiperazine (403 mg, 4.03 mmol) was added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction was confirmed by thin-layer chromatography, the mixture was treated as described above. The residue was purified by silica gel chromatography (chloroform/methanol) to give 5-[5-(4-methylpiperazinyl)methyl[1,3,4]oxadiazol-2-yl]-2-[2-(4-pyridyl)ethylamino]-4-(2-trimethylsilylethoxy)pyrimidine [Compound (IH) in which R2B is 2-(4-pyridyl)ethylamino and —X—Y—Z— is

Workup

  1. additionwas added
  2. customthe reaction mixture was separated
  3. extractionFurther, an aqueous layer was extracted with dichloromethane
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  8. stirringby stirring at room temperature for 12 hours
  9. additionthe mixture was treated
  10. customThe residue was purified by silica gel chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-10da1832cde74a2cbc6f6b3a03d21a80
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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