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

HRID 482268Notes

Reaction equation

HRID 482268 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]>COCCOC>[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

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 98227074-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide2×

Product 1

HCID 676621014-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide hydrochlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4N hydrochloric acid was added dropwise to a stirred suspension of 45.5 g (111.4 mmol) of 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide (compound I) in 810 ml of 1,2-dimethoxyethane at room temperature until the pH was constant at 3.0. 28.4 ml of 4N hydrochloric acid were required for this. The resulting solution was stirred for 30 min (at room temperature) and then evaporated in vacuo. The remaining viscous oily residue was dissolved in 150 ml of boiling acetone, whereupon the formation of a crystalline precipitate immediately started. After cooling in an icebath for 30 min, the crystals were filtered off with suction, washed with acetone and ether and dried at 100° C. in vacuo (180 mbar) for 17 hours. 46.7 g (=94.2% 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. customevaporated in vacuo
  2. dissolutionThe remaining viscous oily residue was dissolved in 150 ml of boiling acetone, whereupon the formation of a crystalline precipitate
  3. temperatureAfter cooling in an icebath for 30 min
  4. filtrationthe crystals were filtered off with suction
  5. washwashed with acetone and ether
  6. customdried at 100° C. in vacuo (180 mbar) for 17 hours

Sources & evidence

ORD record
ord-575eee212eaf4b58b378968e5f6b18f5
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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