Ethyl nitroacetate → 5-Nitro-2-phenylpyrimidin-4(3H)-one

HRID 1740844Notes

Reaction equation

HRID 1740844 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:13])(=[NH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN([CH:17]=[C:18]([N+:24]([O-:26])=[O:25])[C:19](OCC)=[O:20])C.[N+](CC(OCC)=O)([O-])=O.COC(OC)N(C)C>C(O)C>[N+:24]([C:18]1[C:19](=[O:20])[NH:12][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:13][CH:17]=1)([O-:26])=[O:25]

Participants

7

Reactant 5

HCID 69379Ethyl nitroacetateHCID 78373Dimethylformamide dimethyl acetalHCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium MethoxideHCID 54330941ethyl 2-(N,N-dimethylaminomethylene)nitroacetate

Product 1

HCID 135216835-Nitro-2-phenylpyrimidin-4(3H)-oneYield 43.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of sodium methoxide (8 g) and anhydrous ethanol (100 ml) is added benzamidine hydrochloride (11.7 g) at 0° C. The mixture is stirred at 0° C. for 30 minutes, and thereto is added dropwise a solution of crude ethyl 2-(N,N-dimethylaminomethylene)nitroacetate (14 g), which is obtained by refluxing a mixture of ethyl nitroacetate (10 g) and N,N-dimethylformamide dimethyl acetal (10.7 g) for three hours, followed by concentrating the mixture under reduced pressure, in anhydrous ethanol (50 ml) at the same temperature. After addition, the mixture is stirred at room temperature for 30 minutes, and refluxed for 12 hours. The reaction mixture is concentrated under reduced pressure, and water (150 ml) is added to the residue. The pH value of the mixture is adjusted to pH 4 by addition of conc. hydrochloric acid while the mixture is stirred at 0° C. The precipitates are collected by filtration, washed with water, and recrystallized from ethanol to give the desired compound (7 g), m.p. 264-266° C.

Workup

  1. customwhich is obtained
  2. temperatureby refluxing
  3. concentrationby concentrating the mixture under reduced pressure
  4. additionAfter addition
  5. stirringthe mixture is stirred at room temperature for 30 minutes
  6. temperaturerefluxed for 12 hours
  7. concentrationThe reaction mixture is concentrated under reduced pressure, and water (150 ml)
  8. additionis added to the residue
  9. additionThe pH value of the mixture is adjusted to pH 4 by addition of conc. hydrochloric acid while the mixture
  10. stirringis stirred at 0° C
  11. filtrationThe precipitates are collected by filtration
  12. washwashed with water
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-34065f3319bd45eab79776388899e68c
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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