Water → 2-Amino-4-(2,4-dichloro-5-(2,2-diethoxyethoxy)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

HRID 1161737Notes

Reaction equation

HRID 1161737 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([OH:26])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8].O.[CH2:32]([O:34][CH:35]([O:38][CH2:39][CH3:40])[CH2:36]Br)[CH3:33]>C(#N)C>[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([O:26][CH2:36][CH:35]([O:38][CH2:39][CH3:40])[O:34][CH2:32][CH3:33])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 23665647Potassium tert-butoxideHCID 442202982-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Product 1

HCID 442209122-Amino-4-(2,4-dichloro-5-(2,2-diethoxyethoxy)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium tert-butoxide was added to a suspension of 2-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in acetonitrile, bromoacetaldehyde diethyl acetal was added and the suspension heated under reflux for ˜8 hrs. The resulting suspension was allowed to cool and water added, the mixture was extracted with ethyl acetate and the extracts washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a red/brown gum. The crude product was purified by chromatography on silica eluting with mixtures of ethyl acetate and hexane.

Workup

  1. additionwas added
  2. temperaturethe suspension heated
  3. temperatureunder reflux for ˜8 hrs
  4. temperatureto cool
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe extracts washed with water and saturated aqueous sodium chloride solution
  7. dry with materialThe solution was dried over anhydrous sodium sulphate
  8. concentrationconcentrated to a red/brown gum
  9. customThe crude product was purified by chromatography on silica eluting with mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a7f2fda155984f7c9d7715b0f2ad0985
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Reaction notes

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