Hydrochloric Acid → HCID 131716396, compound

HRID 2106781Notes

Reaction equation

HRID 2106781 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]([CH2:46][CH3:47])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40]C(OCC)C)[CH:29]=[C:28]([CH2:48][CH3:49])[N:27]=1.Cl>C(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:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:46][CH3:47])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH:29]=[C:28]([CH2:48][CH3:49])[N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131716398HCID 131716398, compound

Product 1

HCID 131716396HCID 131716396, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was dissolved 4.7 g of dl-5-chloro-6-ethyl-4-[1-ethyl-7-(1-ethoxyethoxy)heptyl]aminopyrimidine, and 10 ml of 1N-HCl was added to the solution and the mixture was refluxed for one hour under stirring After removing ethanol under reduced pressure, the residue was was made alkaline with a sodium hydroxide aqueous solution and was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=2:1) to give 3.8 g of the title compound as pale yellow oily liquid. nD23.0 1.5263.

Workup

  1. additionwas added to the solution
  2. temperaturethe mixture was refluxed for one hour
  3. customAfter removing ethanol under reduced pressure
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1f9beef6eee648568ae436d591b5cb71
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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