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

HRID 482265Notes

Reaction equation

HRID 482265 reaction equation
[C:1]([C:3]([C:16](=[O:29])[N:17]([CH3:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)=[CH:4][NH:5][C:6](=[NH:15])[N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]1=[O:14])#[N:2].O.[OH-].[Na+]>C(O)=O.ClCCl>[CH3:28][N:17]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=1)[C:16]([C:3]1[C:1]([NH2:2])=[N:15][C:6]([N:7]2[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]2=[O:14])=[N:5][CH:4]=1)=[O:29]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178485720HCID 178485720, compound2×

Product 1

HCID 98227074-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)-pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amideYield 56.9%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.634 g (4 mmol) of 1-cyano-1-[N-methyl-N-(3-trifluoromethylphenyl)carbamoyl]-2-[imino(4,4-dimethyl-2-oxo-1-imidazolidinyl)methylamino]ethene (compound IV) in 3 ml of formic acid (98-100% strength) was heated at 50° C. for 2 hours. The formic acid was then stripped off in vacuo, the residue was taken up in dichloromethane, 20 ml of water were added, and the pH was adjusted to between 9 and 10 with dilute sodium hydroxide solution. The organic phase was separated off. The aqueous phase was extracted twice more with dichloromethane. The combined dichloromethane extracts were washed successively with 2 ml of 0.5N NaOH and twice with water, dried with MgSO4 and evaporated in vacuo. The remaining solid residue was mixed with ether/heptane 1:1 and filtered off with suction. After drying (compare Example 13), 0.93 g (=56.9% yield) of pure 4-amino-2-(4,4-dimethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl) amide was obtained, melting point 210°-211° C.; TLC in CH2Cl2 /C2 H5OH=10:1.

Workup

  1. customThe organic phase was separated off
  2. extractionThe aqueous phase was extracted twice more with dichloromethane
  3. washThe combined dichloromethane extracts were washed successively with 2 ml of 0.5N NaOH and twice with water
  4. dry with materialdried with MgSO4
  5. customevaporated in vacuo
  6. additionThe remaining solid residue was mixed with ether/heptane 1:1
  7. filtrationfiltered off with suction
  8. customAfter drying (compare Example 13)

Sources & evidence

ORD record
ord-ab8fd93d1c0849578b9e21500b9d7500
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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