m-Chloroperbenzoic acid → HCID 46908598, compound

HRID 1616100Notes

Reaction equation

HRID 1616100 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][S:4][C:5]1[N:10]=[C:9]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>C(Cl)(Cl)Cl>[F:23][C:2]([F:1])([F:22])[CH2:3][S:4]([C:5]1[N:10]=[C:9]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)=[O:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66776407HCID 66776407, compound

Product 1

HCID 46908598HCID 46908598, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-[2-(2,2,2-Trifluoro-ethylsulfanyl)-pyrimidin-4-yl]-3H-quinazolin-4-one (1.1 g, 3.25 mmol) was dissolved in 20 mL chloroform, and m-chloroperoxybenzoic acid (m-CPBA) (0.7 g, 3.57 mmol, 85% of purity) was added at room temperature. The reaction mixture was stirred for 3 hours at room temperature. Washing with sodium-thiosulfate solution and sodium-hydrogencarbonate, drying with Na2SO4 and the crude product was purified by prep-TLC and then prep-HPLC to give 3-[2-(2,2,2-trifluoro-ethylsulfinyl)pyrimidin-4-yl]-3H-quinazolin-4-one (0.35 g, 30.5%) as an off-white solid.

Workup

  1. washWashing with sodium-thiosulfate solution and sodium-hydrogencarbonate
  2. dry with materialdrying with Na2SO4
  3. customthe crude product was purified by prep-TLC and then prep-HPLC

Sources & evidence

ORD record
ord-5ee9a9580a7e4e5884b4e9139bcb5e05
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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