Acetic Acid → HCID 22611712, compound

HRID 565716Notes

Reaction equation

HRID 565716 reaction equation
C(O)(=O)C.O.[CH2:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]2)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C.ClCCl.[Fe]>[NH2:20][C:19]1[C:14]([NH:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:15][C:16]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22611715HCID 22611715, compound

Product 1

HCID 22611712HCID 22611712, compoundYield 68.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.3 ml of acetic acid, 1.3 ml of distilled water and 1.40 g of iron were added to a suspension of 0.90 g of ethyl 1-[4-benzylamino-5-nitropyrimidin-2-yl)-4-piperidinecarboxylate (Reference Example 6) in 50 ml of ethanol and the reaction solution was refluxed for 5 hours. The dark blue solution was filtered to remove the insoluble substance, and concentrated under reduced pressure to obtain the thin yellow oily product. The resulting product was dissolved in dichloromethane and washed with 10% sodium carbonate(50 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.57 g of the title compound as a oily product.

Workup

  1. temperaturethe reaction solution was refluxed for 5 hours
  2. filtrationThe dark blue solution was filtered
  3. customto remove the insoluble substance
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the thin yellow oily product
  6. washwashed with 10% sodium carbonate(50 ml×2)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5717487f64d4d33af96dccedaa7c26d
Source dataset
uspto-grants-2001_01
Patent number
US06172227B2

Reaction notes

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