Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[C:27]([O-])(=[O:30])[CH2:28][OH:29].[Na+].[Na]>C(O)CO>[OH:29][CH2:28][CH2:27][O:30][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1Participants
5
Procedure
190 mg of N-[6-chloro-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfonamide were added to a sodium glycolate solution from 46 mg of sodium in 1 ml of ethylene glycol. After a reaction period of 5 hours at 100° C., the reaction mixture was evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase was washed neutral, dried and evaporated under reduced pressure. The residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v). There were obtained 175 mg of N-[6-(2-hydroxy-ethoxy)-5-(p-methoxyphenyl)-4-pyrimidinyl]-p-toluenesulfon-amide, melting point 147°-149° C. (from methylene chloride/hexane).
Workup
- customAfter a reaction period of 5 hours at 100° C.
- customthe reaction mixture was evaporated to dryness under reduced pressure
- customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
- washThe organic phase was washed neutral
- customdried
- customevaporated under reduced pressure
- customThe residue was chromatographed on silica gel with methylene chloride and ethyl acetate (4:1 v/v)
Sources & evidence
- ORD record
- ord-e2b486f0faba44978e09600883630e9b
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05270313
Linked notes
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