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

HRID 237383Notes

Reaction equation

HRID 237383 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-911bb7f0d82249858749c073e58eb851
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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