Stannous chloride dihydrate → HCID 69145927, compound

HRID 2251810Notes

Reaction equation

HRID 2251810 reaction equation
O.O.[Sn](Cl)Cl.[CH2:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=2)[CH2:11][CH2:10]1)[CH:7]=[CH2:8]>CO>[CH2:6]([N:9]1[CH2:10][CH2:11][N:12]([C:15]2[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=2)[CH2:13][CH2:14]1)[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69146013HCID 69146013, compound

Product 1

HCID 69145927HCID 69145927, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.84 g (17.0 mmol) of tin(II) chloride dihydrate were added to a solution of 530 mg (2.13 mmol) of 2-(4-allylpiperazin-1-yl)-5-nitropyrimidine from Example 16.1 in 20 ml of methanol and, after that, the reaction mixture was heated at reflux for 1 hour. After the solvent had been evaporated to dryness, the residue was treated with saturated aqueous sodium chloride solution and then made alkaline using dilute aqueous sodium hydroxide solution. After that, the aqueous reaction mixture was extracted with ethyl acetate. The solid which had precipitated out was filtered off with suction. The phases were then separated and the aqueous phase was extracted in each case twice with ethyl acetate and dichloromethane. After the combined organic phases had been dried over sodium sulfate, the drying agent had been filtered off and the solvent had been evaporated down to dryness, 220 mg (46% of theory) of the title compound were obtained.

Workup

  1. temperatureafter that, the reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customAfter the solvent had been evaporated to dryness
  4. additionthe residue was treated with saturated aqueous sodium chloride solution
  5. extractionAfter that, the aqueous reaction mixture was extracted with ethyl acetate
  6. customThe solid which had precipitated out
  7. filtrationwas filtered off with suction
  8. customThe phases were then separated
  9. extractionthe aqueous phase was extracted in each case twice with ethyl acetate and dichloromethane
  10. dry with materialAfter the combined organic phases had been dried over sodium sulfate
  11. filtrationthe drying agent had been filtered off
  12. customthe solvent had been evaporated down to dryness, 220 mg (46% of theory) of the title compound
  13. customwere obtained

Sources & evidence

ORD record
ord-b476a6a1eb5a4343b403bbbdbd3bbd04
Source dataset
uspto-grants-2008_01
Patent number
US07320979B2

Reaction notes

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