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

HRID 1161744Notes

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

Participants

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

temperatureto cool
washthe mixture was washed with water and saturated aqueous sodium chloride solution
dry with materialThe solution was dried over anhydrous sodium sulphate
concentrationconcentrated to a pale yellow solid
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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