Toluene → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-difluoropropoxy)benzyl]aminopyrimidine

HRID 330317Notes

Reaction equation

HRID 330317 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]([CH2:47][CH3:48])[C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41](F)(F)[CH:42]([F:44])[F:43])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:49][CH3:50])[N:27]=1.[CH2:51](N(S(F)(F)F)CC)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1C=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]([CH2:47][CH3:48])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]([F:44])([F:43])[CH3:51])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:49][CH3:50])[N:27]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluorideHCID 131716271DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(1,1,2,2-tetrafluoroethoxy)benzyl]aminopyrimidine

Product 1

HCID 131716275DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-difluoropropoxy)benzyl]aminopyrimidineYield 61.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 1.0 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-acetonyloxybenzyl)aminopyrimidine obtained in Example 17 dissolved in 50 ml of dried benzene was added 0.5 g of diethylaminosulfur trifluoride, and the mixture was refluxed by heating for 5 hours while stirring. After completion of the reaction, the mixture was poured into ice-cold water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent 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 oily liquid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. customAfter completion of the reaction
  4. additionthe mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe oily product obtained

Sources & evidence

ORD record
ord-257f3afcb0c547779fb6655c55197a2a
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

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