Water → HCID 59253663, compound

HRID 2194962Notes

Reaction equation

HRID 2194962 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:24]([O:26]CC)=[O:25])=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+].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)[C:15]([C:24]([OH:26])=[O:25])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 592536665-Pyrimidinecarboxylic acid, 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)-, ethyl ester

Product 1

HCID 59253663HCID 59253663, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

23 g ethyl 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)pyrimidine-5-carboxylate and 19 g sodium carbonate in a mixture composed by 150 mL water and 150 mL ethanol is suspended. It is refluxed for three hours distilling the ethanol, and compensating with water the volume loss. Once completed the conversion, it is cooled to 50° C. and adjusted to pH 6 with acetic acid. The suspension is filtrated, yielding, upon drying, 20 g of product with HPLC purity of 95% (A %), which is identified through 1H-NMR.

Workup

  1. temperatureIt is refluxed for three hours
  2. distillationdistilling the ethanol
  3. filtrationThe suspension is filtrated
  4. customyielding
  5. customupon drying

Sources & evidence

ORD record
ord-233f595da26147b7b38c56ba1a64559e
Source dataset
uspto-grants-2012_12
Patent number
US08334381B2

Reaction notes

Loading…