Sodium → 2-Nitroamino-5-(4-pyridyl)methyl-4-pyrimidone

HRID 358481Notes

Reaction equation

HRID 358481 reaction equation
[Na].C[O-].[Na+].[N+:5]([NH:8][C:9]([NH2:11])=[NH:10])([O-:7])=[O:6].[CH:12]([CH:14]([CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[C:15](OCC)=O)=[O:13]>CO>[N+:5]([NH:8][C:9]1[NH:11][C:12](=[O:13])[C:14]([CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:15][N:10]=1)([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 20448164Ethyl 2-formyl-3-(4-pyridyl)propionateHCID 86287517Nitroguanidine

Product 1

HCID 133734742-Nitroamino-5-(4-pyridyl)methyl-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

About 1.77 g. of sodium were dissolved in 75 ml. of anhydrous methanol under a positive nitrogen atmosphere. The sodium methoxide in methanol solution was cooled and 7.28 g. of dried nitroguanidine added thereto. The reaction mixture was heated to reflux temperature briefly after which time 14.5 g. of ethyl 2-formyl-3-(4-pyridyl)propionate (prepared by the method of U.S. Pat. No. 4,216,318) were added thereto. This reaction mixture was then heated to refluxing temperature for about 19 hours. Volatile constituents were removed by evaporation and water was added to the residue. The aqueous mixture was extracted 3 times with chloroform and the chloroform extracts discarded. The aqueous solution was then chilled to about 0° C. and 15.4 ml. of 5N aqueous hydrochloric acid added. 2-Nitroamino-5-(4-pyridyl)methyl-4-pyrimidone formed in the above reaction precipitated and the precipitate was collected by filtration. The filter cake was washed with water and dried. 9.9 g. of product were obtained melting at about 228°-229° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature briefly after which time 14.5 g
  3. addition4,216,318) were added
  4. temperatureThis reaction mixture was then heated
  5. temperatureto refluxing temperature for about 19 hours
  6. customVolatile constituents were removed by evaporation and water
  7. additionwas added to the residue
  8. extractionThe aqueous mixture was extracted 3 times with chloroform
  9. additionof 5N aqueous hydrochloric acid added

Sources & evidence

ORD record
ord-f9e1c6de094b4caa97ae95b9ff6e7d48
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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