Water → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 1920041Notes

Reaction equation

HRID 1920041 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15](C(OCC)=O)=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 592536665-Pyrimidinecarboxylic acid, 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)-, ethyl ester

Product 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

140 g ethyl 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)pyrimidine-5-carboxylate and 109 g potassium carbonate is suspended in a mixture composed by 1050 mL water and 560 mL ethanol. The mixture is refluxed for 1 hour, then 700 mL solvent are slowly distilled. Once completed the conversion, the mixture is cooled to 80° C. and it is adjusted to pH a 7 with 95 mL acetic acid. 560 mL N-methylpyrrolidone and 0.9 g CuO is added. The water present is distilled under reduced pressure, and the mixture is heated to 175-180° C. for 2 hours. Once completed the conversion, the mixture is cooled to 80-90° C., 1000 mL water and 5 g EDTA is slowly added, the mixture is stirred at room temperature, the product is filtrated and washed with water. Upon drying, 108 g of product with HPLC purity of 95% (A %) is achieved. This can be recrystallized from 10 volumes of 95:5 xylene/N-methylpyrrolidone to yield a product with 98% purity (A %) in a 80% yield.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. distillation700 mL solvent are slowly distilled
  3. addition560 mL N-methylpyrrolidone and 0.9 g CuO is added
  4. distillationThe water present is distilled under reduced pressure
  5. temperaturethe mixture is heated to 175-180° C. for 2 hours
  6. temperaturethe mixture is cooled to 80-90° C.
  7. addition1000 mL water and 5 g EDTA is slowly added
  8. filtrationthe product is filtrated
  9. washwashed with water
  10. customUpon drying
  11. customThis can be recrystallized from 10 volumes of 95:5 xylene/N-methylpyrrolidone
  12. customto yield a product with 98% purity (A %) in a 80% yield

Sources & evidence

ORD record
ord-ba6f99775e334ccc901a2213c9d8afab
Source dataset
uspto-grants-2012_05
Patent number
US08168787B2

Reaction notes

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