p-Toluenesulfonic acid monohydrate → 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide p-toluenesulfonate

HRID 482270Notes

Reaction equation

HRID 482270 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][N:14]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=1)[C:15]([C:17]1[C:18]([NH2:31])=[N:19][C:20]([N:23]2[CH2:27][C:26]([CH3:29])([CH3:28])[NH:25][C:24]2=[O:30])=[N:21][CH:22]=1)=[O:16]>C(#N)C>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[CH3:13][N:14]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:39])[F:41])[CH:33]=1)[C:15]([C:17]1[C:18]([NH2:31])=[N:19][C:20]([N:23]2[CH2:27][C:26]([CH3:29])([CH3:28])[NH:25][C:24]2=[O:30])=[N:21][CH:22]=1)=[O:16]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 98227074-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide

Product 1

HCID 867530304-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide p-toluenesulfonateYield 94.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 285.5 mg (1.5 mmol) of p-toluenesulfonic acid hydrate in 10 ml of acetonitrile was added to a suspension of 613 mg (1.5 mmol) of compound I in 4 ml of acetonitrile at room temperature. The resulting solution (pH 3-4) was stirred at room temperature for 20 min and evaporated in vacuo. Ether was added to the residue. This resulted in crystallization of a substance which, after stirring at room temperature for 20 min, was filtered off with suction and washed with ether. Drying (5-6 mbar, 80° C., 8 hours) resulted in 820 mg (=94.1% yield) of pure 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide p-toluenesulfonate, melting point 168°-170° C.

Workup

  1. customevaporated in vacuo
  2. additionEther was added to the residue
  3. customThis resulted in crystallization of a substance which
  4. filtrationwas filtered off with suction
  5. washwashed with ether
  6. customDrying (5-6 mbar, 80° C., 8 hours)

Sources & evidence

ORD record
ord-09ea602360d64fa28c8ee31ae710b357
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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