Water → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(3-pyridyloxy)benzyl]aminopyrimidine

HRID 330312Notes

Reaction equation

HRID 330312 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.Br[C:47]1[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=1.O.C1(C)C=CC=CC=1>N1C=CC=CC=1.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:47]3[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=3)=[CH:37][CH:36]=2)[CH:30]=[C:29]([CH2:44][CH3:45])[N:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 122863-BromopyridineHCID 131716264DL-5 Chloro-6-ethyl-4-(alpha-ethyl-4-hydroxybenzyl)aminopyrimidine sodium salt

Product 1

HCID 131716262DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(3-pyridyloxy)benzyl]aminopyrimidineYield 33.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 2.2 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine sodium salt dissolved in 25 ml of dried pyridine were added 1.1 g of 3-bromopyridine and 1 g of cuprous chloride, and the mixture was refluxed under nitrogen atmosphere by heating and stirring for 8 hours. After completion of the reaction, the reaction product was poured into water and extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid and water, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The oily product obtained was isolated by chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=4:1) to give 0.8 g of the desired product as colorless oily liquid.

Workup

  1. temperaturethe mixture was refluxed under nitrogen atmosphere
  2. temperatureby heating
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with diluted hydrochloric acid and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe oily product obtained

Sources & evidence

ORD record
ord-c158d20b11164b78a142cb1a49dd7619
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

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