Hydrogen Peroxide → 6-Amino-5-chloro-2-(4-chloro-2-fluoro-3-methanesulfinylphenyl)pyrimidine-4-carboxylic acid methyl ester

HRID 1363945Notes

Reaction equation

HRID 1363945 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([NH2:12])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([S:20][CH3:21])[C:14]=2[F:22])[N:6]=1)=[O:4].OO.S([O-])([O-])=[O:26].[Na+].[Na+]>C(O)C(F)(F)F>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([NH2:12])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([S:20]([CH3:21])=[O:26])[C:14]=2[F:22])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 669536876-Amino-5-chloro-2-(4-chloro-2-fluoro-3-methylthio-phenyl)pyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 669537416-Amino-5-chloro-2-(4-chloro-2-fluoro-3-methanesulfinylphenyl)pyrimidine-4-carboxylic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

6-Amino-5-chloro-2-(4-chloro-2-fluoro-3-methylthio-phenyl)pyrimidine-4-carboxylic acid methyl ester (2.4 g, 6.63 mmol) was dissolved with heating in a minimum amount of trifluoroethanol (50 mL). After allowing the reaction mixture to cool to room temperature, 30% hydrogen peroxide (3.0 mL, 26.5 mmol) was added and the reaction mixture was stirred for 2 days. An aqueous solution of sodium sulfite (10% solution) was added to quench excess oxidant (exotherm noted) and the reaction mixture was stirred for 1 hour. Additional water was then added and the reaction mixture was filtered. The precipitate was found to be pure 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methanesulfinylphenyl)pyrimidine-4-carboxylic acid methyl ester (2.13 g, 85% yield): mp 256-258° C.: 1H NMR (CDCl3): δ 8.03 (dd, 1H), 7.54 (dd, 1H), 3.92 (s, 3H), 3.13 (s, 3H).

Workup

  1. customto quench excess oxidant (exotherm noted)
  2. stirringthe reaction mixture was stirred for 1 hour
  3. additionAdditional water was then added
  4. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-0e6dfbc5fdca4b8780b81cce9abb5d9b
Source dataset
uspto-grants-2011_02
Patent number
US07888287B2

Reaction notes

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