Acetic Acid → HCID 22611712, compound

HRID 843654Notes

Reaction equation

HRID 843654 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 are added to a suspension of 0.90 g of ethyl 1-(4-benzylamino-5-nitropyrimidine-2-yl)-4-piperidinecarboxylate (Reference Example 6) in 50 ml of ethanol, and the reaction solution is refluxed for 5 hours. The dark blue solution is 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 is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.57 g of the title compound as an oily product.

Workup

  1. temperaturethe reaction solution is refluxed for 5 hours
  2. filtrationThe dark blue solution is 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 is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6db8220310f4126b67c287decdd6441
Source dataset
uspto-grants-2002_04
Patent number
US06380206B1

Reaction notes

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