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

HRID 1898927Notes

Reaction equation

HRID 1898927 reaction equation
[C:1]([C:3]([C:16](=[O:32])[N:17]([CH2:28]C1CC1)[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](C)([CH3:12])[NH:9][C:8]1=[O:14])#[N:2].[C:33](O)(=O)[C:34](O)=O.[C:39](O)(=O)C>>[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]([CH2:12][CH3:39])([CH2:33][CH3:34])[NH:9][C:8]2=[O:14])=[N:5][CH:4]=1)=[O:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 971Oxalic AcidHCID 178428592HCID 178428592, compound

Product 1

HCID 536804274-amino-2-(4,4-diethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amideYield 64.6%

Procedure

A mixture of 2.80 g (6.41 mmol) of a compound II (R1, R2 =C2H5 ; R3, R5, R6 =H; R4 =CH3), 210 mg of anhydrous oxalic acid and 4.75 ml of glacial acetic acid was stirred at 70° for 2.5 hours, a solution being produced after 20 min. It was then evaporated in vacuo. The residue was taken up in 70 ml of CH2Cl2 and extracted three times in succession with 20 ml of N NaOH each time and then twice with 20 ml of water each time. The CH2Cl2 solution was dried with MgSO4, filtered and evaporated in vacuo. The residue was taken up in about 15 ml of ether, whereupon crystallization occurred. The crystalline product was filtered off with suction and washed with ether and dried in vacuo at 100° for 17 hours. 1.81 g (=64.6% yield) of pure 4-amino-2-(4,4-diethyl-2-oxo-1-imidazolidinyl)pyrimidine-5-carboxylic acid N-methyl-N-(3-trifluoromethylphenyl)amide were obtained, melting point 185°-187°. C20H23F3N6O2 (436.45) Calculated: C 55.04 H 5.31 N 19.26% Found: C 54.8 H 5.2 N 19.2

Workup

  1. customa solution being produced after 20 min
  2. customIt was then evaporated in vacuo
  3. extractionextracted three times in succession with 20 ml of N NaOH each time
  4. dry with materialThe CH2Cl2 solution was dried with MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was taken up in about 15 ml of ether, whereupon crystallization
  8. filtrationThe crystalline product was filtered off with suction
  9. washwashed with ether
  10. customdried in vacuo at 100° for 17 hours

Sources & evidence

ORD record
ord-78f01bc9d6a14dee84d915b5c9122f80
Source dataset
uspto-grants-1996_11
Patent number
US05571816

Reaction notes

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