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Ethyl Acetate → C-[2-Amino-6-(2,4-dimethylphenyl)-5-formyl-pyrimidin-4-ylsulphanyl]-N-cyclopropyl-methane sulphonamide

HRID 1161744
Notes
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Reaction equation

HRID 1161744 reaction equation
C(=O)([O-])O.[Na+].[NH2:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH3:20])[C:10]([CH:21]=[O:22])=[C:9]([SH:23])[N:8]=1.Br[CH2:25][S:26]([NH:29][CH:30]1[CH2:32][CH2:31]1)(=[O:28])=[O:27].C(OCC)(=O)C>CN(C=O)C>[NH2:6][C:7]1[N:8]=[C:9]([S:23][CH2:25][S:26]([NH:29][CH:30]2[CH2:32][CH2:31]2)(=[O:28])=[O:27])[C:10]([CH:21]=[O:22])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH3:20])[N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 68594886C-bromo-N-cyclopropyl-methane sulphonamideHCID 178423997HCID 178423997, compound

Product 1

HCID 59519319C-[2-Amino-6-(2,4-dimethylphenyl)-5-formyl-pyrimidin-4-ylsulphanyl]-N-cyclopropyl-methane sulphonamide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
85 °C

Procedure

Sodium hydrogen carbonate was added to a solution of 2-Amino-4-(2,4-dimethylphenyl)-6-mercapto-pyrimidine-5-carbaldehyde in DMF and the suspension stirred. C-bromo-N-cyclopropyl-methane sulphonamide was added, and the mixture heated, ˜85° C., for ˜3 hrs. The resulting suspension was allowed to cool and ethyl acetate added, the mixture was washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a pale yellow solid. The crude solid was purified by column chromatography on silica eluting with mixtures of ethyl acetate and hexane.

Workup

  1. temperatureto cool
  2. washthe mixture was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialThe solution was dried over anhydrous sodium sulphate
  4. concentrationconcentrated to a pale yellow solid
  5. customThe crude solid was purified by column chromatography on silica eluting with mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3059699036b64a0fba3385c698b265ff
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820658B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes