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

HRID 330315Notes

Reaction equation

HRID 330315 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.[Na].[F:46][C:47]([F:51])=[C:48]([F:50])[F:49].O>CN(C)C=O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[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]([F:50])([F:49])[CH:47]([F:51])[F:46])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8301TetrafluoroethyleneHCID 5360545SodiumHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131716271DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(1,1,2,2-tetrafluoroethoxy)benzyl]aminopyrimidineYield 32.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 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-78009be601574729950eace4603f2f7e
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

Loading…