1,3-Dimethyl-2-imidazolidinone → DL-5 Chloro-6-ethyl-4-{alpha-ethyl-4-(4-cyano-2,3,5,6-tetrafluorophenoxy) benzylamino}pyrimidine

HRID 847373Notes

Reaction equation

HRID 847373 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]([C:52]#[N:53])=[C:50]([F:54])[C:49]([F:55])=[C:48](F)[C:47]=1[F:57].C(=O)([O-])[O-].[K+].[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:48]3[C:47]([F:57])=[C:46]([F:45])[C:51]([C:52]#[N:53])=[C:50]([F:54])[C:49]=3[F:55])=[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 11430Potassium CarbonateHCID 69882PentafluorobenzonitrileHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131717497DL-5 Chloro-6-ethyl-4-{alpha-ethyl-4-(4-cyano-2,3,5,6-tetrafluorophenoxy) benzylamino}pyrimidineYield 82.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.76 g of dl-5-chloro-6-ethyl-4-(αethyl-4-hydroxybenzylamino)pyrimidine, 0.5 g of pentafluorobenzonitrile, 0.4 g of anhydrous potassium carbonate 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=10:1) to give 0.8 g of the desired product as a colorless oily product.

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-55c7dc7f75bb4437b862faf7e8a13ee0
Source dataset
uspto-grants-1992_08
Patent number
US05141941

Reaction notes

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