MeOH tetrahydrofuran → Methyl 2-(methylsulfonyl)pyrimidine-4-carboxylate

HRID 1581523Notes

Reaction equation

HRID 1581523 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

Reactant 3

HCID 21899815MeOH tetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 692220192-Methyl-sulfanyl-pyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 19868790Methyl 2-(methylsulfonyl)pyrimidine-4-carboxylate

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

  1. customThe resulting suspension is partitioned between methylene chloride and water
  2. additionwith the addition of NaOH and re
  3. extractionextracted with solvent
  4. customThe combined organic layers are dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17e4af372e4346f2ac5c06e1cb231206
Source dataset
uspto-grants-2004_05
Patent number
US06730668B2

Reaction notes

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