m-Chloroperbenzoic acid → Ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate

HRID 2200903Notes

Reaction equation

HRID 2200903 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]([S:18][CH3:19])[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]([S:18]([CH3:19])=[O:33])[N:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118157383Ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

Product 1

HCID 118157877Ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In DCM (50 mL) was dissolved ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate (2.2 g, 6.3 mmol). m-CPBA (3-chloroperbenzoic acid, 1.1 g, 6.4 mmol) was added. The reaction was conducted at ambient temperature for 30 min. The reaction mixture was washed with water. The organic phase was dried over sodium sulfate and concentrated to give ethyl 4-((3-fluoro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate. The product was used in the subsequent procedure without further purification.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75c1df15842f4cc2a8d0c8774f2bba32
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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