m-Chloroperbenzoic acid → 6-bromo-8-isopropyl-4-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 641647Notes

Reaction equation

HRID 641647 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]([CH3:18])[CH3:17])[C:5]2[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]([CH3:18])[CH3:17])[C:5]2[N:6]=[C:7]([S:11]([CH3:12])=[O:27])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 592589536-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 592589926-bromo-8-isopropyl-4-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (−20° C.) solution of 6-bromo-8-isopropyl-4-methyl-2-(methylthio)-pyrido[2,3-d]pyrimidin-7(8H)-one (380 mg, 1.16 mmol) in CH2Cl2 (25 mL) was added MCPBA (340 mg, 77%, 1.52 mmol). After stirring for 30 min (−20° C. to 0° C.), the mixture was quenched with saturated aqueous NaHCO3, extracted with EtOAc, dried and evaporated. The crude product was washed with EtOAc/Hexane to give the title compound (190 mg, 48%).

Workup

  1. stirringAfter stirring for 30 min (−20° C. to 0° C.)
  2. customthe mixture was quenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. customdried
  5. customevaporated
  6. washThe crude product was washed with EtOAc/Hexane

Sources & evidence

ORD record
ord-d2c0ce1c8e2141b8b028716dfd590fc7
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

Loading…