Water → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(1,1,2,2-tetrafluoroethoxy)benzyl]aminopyrimidine

HRID 703863Notes

Reaction equation

HRID 703863 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].[Na].[Cl:26][C:27]1[N:32]=[C:31]([NH:33][CH:34]([CH2:42][CH3:43])[C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[CH:30]=[C:29]([CH2:44][CH3:45])[N:28]=1.[F:46][C:47]([F:51])=[C:48]([F:50])[F:49].O.C1(C)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[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:26][C:27]1[N:32]=[C:31]([NH:33][CH:34]([CH2:42][CH3:43])[C:35]2[CH:40]=[CH:39][C:38]([O:41][C:48]([F:50])([F:49])[CH:47]([F:51])[F:46])=[CH:37][CH:36]=2)[CH:30]=[C:29]([CH2:44][CH3:45])[N:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8301TetrafluoroethyleneHCID 131716264DL-5 Chloro-6-ethyl-4-(alpha-ethyl-4-hydroxybenzyl)aminopyrimidine sodium salt

Product 1

HCID 131716271DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(1,1,2,2-tetrafluoroethoxy)benzyl]aminopyrimidineYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of 1.6 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine sodium salt dissolved in 30 ml of N,N-dimethylformamide was gradually bubbled about 2.2 g of tetrafluoroethylene at 80° C. under nitrogen atmosphere while stirring. After completion of the bubbling, the mixture was stirred for 2 hours, and the reaction mixture was charged into water and separated oily product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and ethyl acetate was distilled off under reduced pressure. The oily product obtained was isolated by column chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=7:1) to give 0.6 g of the desired product as pale yellow liquid.

Workup

  1. customat 80° C.
  2. stirringAfter completion of the bubbling, the mixture was stirred for 2 hours
  3. customseparated oily product
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate and ethyl acetate
  7. distillationwas distilled off under reduced pressure
  8. customThe oily product obtained

Sources & evidence

ORD record
ord-a96fc8320b7e4121a7dd31abfda66425
Source dataset
uspto-grants-1991_01
Patent number
US04985426

Reaction notes

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