Reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7][O:8][C:9]([C:11]1[C:16](S)=[CH:15][N:14]=[C:13](C)[N:12]=1)=[O:10].CO.[CH2:21]1COCC1>>[CH3:7][O:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:3]([CH3:21])(=[O:5])=[O:2])[N:12]=1)=[O:10]Participants
4
Procedure
An aqueous solution (1 L) of Oxone® (211.7 g, 344 mmol) is added dropwise at 0° C. to a solution of 2-methyl-sulfanyl-pyrimidine-4-carboxylic acid methyl ester, 14, (19 g, 86.1 mmol) in 1:1 methanol/THF (1 L). The reaction solution is allowed to warm to room temperature and stir for 1.5 hours. The resulting suspension is partitioned between methylene chloride and water. The aqueous phase is made alkaline with the addition of NaOH and re extracted with solvent. The combined organic layers are dried, filtered, and concentrated in vacuo to afford 18.4 g of the desired product as a yellow oil.
Workup
- customThe resulting suspension is partitioned between methylene chloride and water
- additionwith the addition of NaOH and re
- extractionextracted with solvent
- customThe combined organic layers are dried
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f8a5879afc274fa58e6da378bb496052
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960593B2
Linked notes
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