1,3-Dimethyl-2-imidazolidinone → HCID 131717499, compound

HRID 847374Notes

Reaction equation

HRID 847374 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.[F:45][C:46]1[C:51]([F:52])=[C:50](F)[C:49]([F:54])=[C:48]([F:55])[C:47]=1[C:56]([F:59])([F:58])[F:57].[OH-].[K+].CN1CCN(C)C1=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([O:40][C:50]3[C:49]([F:54])=[C:48]([F:55])[C:47]([C:56]([F:57])([F:59])[F:58])=[C:46]([F:45])[C:51]=3[F:52])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

8

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 9906OctafluorotolueneHCID 14797Potassium HydroxideHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131717499HCID 131717499, compoundYield 111.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzylamino)pyrimidine, 1 g of perfluorotoluene, 0.24 g of powdery potassium hydroxide and 20 ml of 1,3-dimethyl-2-imidazolidinone (DMI) was heated under stirring at 70° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into water, and extracted with toluene. The extract was washed with water, dried over anhydrous sodium sulfate and then toluene was evaporated under reduced pressure. The oily product obtained was isolated by column chromatography (Wako gel C-200, eluted with toluene:ethyl acetate=30:1) to give 1.5 g of the desired product as colorless crystals.

Workup

  1. temperaturewas heated
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customtoluene was evaporated under reduced pressure
  7. customThe oily product obtained

Sources & evidence

ORD record
ord-fae56da5724e44ad83bde53adc3f8250
Source dataset
uspto-grants-1992_08
Patent number
US05141941

Reaction notes

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