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

HRID 482269Notes

Reaction equation

HRID 482269 reaction equation
[ClH:1].[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)[C:4]([C:6]1[C:7]([NH2:20])=[N:8][C:9]([N:12]2[CH2:16][C:15]([CH3:18])([CH3:17])[NH:14][C:13]2=[O:19])=[N:10][CH:11]=1)=[O:5]>CCOCC.C(OCC)(=O)C.CO>[ClH:1].[CH3:2][N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=1)[C:4]([C:6]1[C:7]([NH2:20])=[N:8][C:9]([N:12]2[CH2:16][C:15]([CH3:18])([CH3:17])[NH:14][C:13]2=[O:19])=[N:10][CH:11]=1)=[O:5]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 98227074-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide

Product 1

HCID 676621014-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide hydrochlorideYield 92.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an analogous manner to the description in Example 22, 1.35 ml of a 6.6 molar solution of HCl in ether were added to a solution of 8 mmol of the compound I in 25 ml of ethyl acetate and 5 ml of methanol, and the mixture was then evaporated in vacuo. The viscous oily residue was dissolved in 20 ml of boiling acetone, whereupon a crystalline precipitate separated out after a few minutes. After stirring while cooling in an icebath for 30 min, the solid was filtered off with suction, washed with acetone and ether and dried as described in Example 13. 3.28 g (92.3% yield) of pure 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide hydrochloride were obtained, melting point 210°-211° C.

Workup

  1. customthe mixture was then evaporated in vacuo
  2. dissolutionThe viscous oily residue was dissolved in 20 ml of boiling acetone, whereupon a crystalline precipitate
  3. customseparated out after a few minutes
  4. temperaturewhile cooling in an icebath for 30 min
  5. filtrationthe solid was filtered off with suction
  6. washwashed with acetone and ether
  7. customdried

Sources & evidence

ORD record
ord-d6aad7411ae0461bbb780e9f90be9351
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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