Sodium Hydroxide → 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide

HRID 482267Notes

Reaction equation

HRID 482267 reaction equation
Cl.[C:2]([C:4]([C:17](=[O:30])[N:18]([CH3:29])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)=[CH:5][NH:6][C:7](=[NH:16])[N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]1=[O:15])#[N:3].[OH-].[Na+].C(OCC)C.C(OC(C)C)(C)C>>[CH3:29][N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=1)[C:17]([C:4]1[C:2]([NH2:3])=[N:16][C:7]([N:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]2=[O:15])=[N:6][CH:5]=1)=[O:30]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21919906Ether isopropyl etherHCID 178485721HCID 178485721, compound

Product 1

HCID 98227074-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amideYield 32.6%

Procedure

2.67 g (6 mmol) of 1-cyano-1-[N-methyl-N-(3-trifluoromethylphenyl)carbamoyl]-2-[imino(4,4-dimethyl-2-oxo-1-imidazolidinyl)methylamino]ethene hydrochloride are heated at 187°-189° C. under vacuum (4-6 mbar) for 10 min in a bath preheated to 190° C. After cooling, the solidified melt was mixed with 5 ml of 2N sodium hydroxide solution. 12 ml of diethyl ether/diisopropyl ether 5:1 were added. Stirring resulted in initial formation of two clear phases, from which crystals separated out. The mixture was stirred while cooling in ice for 1 hour, and the crystals were filtered off with suction, washed with water and taken up in 50 ml of CH2Cl2. The solution which formed was extracted successively three times with 5 ml of 0.5N NaOH each time and twice with 5 ml of water each time, dried over Na2SO4, filtered and evaporated. The residue was triturated with diisopropyl ether, filtered off with suction and dried as in Example 13. 0.82 g (=32.6% yield) of the compound I was obtained, melting point 209°-210° C.

Workup

  1. custompreheated to 190° C
  2. temperatureAfter cooling
  3. customresulted in initial formation of two clear phases
  4. customfrom which crystals separated out
  5. stirringThe mixture was stirred
  6. temperaturewhile cooling in ice for 1 hour
  7. filtrationthe crystals were filtered off with suction
  8. washwashed with water
  9. customThe solution which formed
  10. extractionwas extracted successively three times with 5 ml of 0.5N NaOH each time
  11. dry with materialtwice with 5 ml of water each time, dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue was triturated with diisopropyl ether
  15. filtrationfiltered off with suction
  16. customdried as in Example 13

Sources & evidence

ORD record
ord-0041f9b857494f3aacff20c2f001cc3e
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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