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

HRID 387225Notes

Reaction equation

HRID 387225 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH2:21][CH3:22])[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:4]([Cl:23])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH2:21][CH3:22])[C:11]3[N:12]=[C:13]([S:16]([CH3:17])=[O:32])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:4]([Cl:23])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 671196406-(4-Bromo-2-chlorophenyl)-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 671196546-(4-bromo-2-chlorophenyl)-8-ethyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-(4-bromo-2-chlorophenyl)-8-ethyl-2-(methylthio)-pyrido[2,3-d]pyrimidin-7(8H)-one (10, 1.30 g, 3.16 mmol) in dichloromethane (20 mL) was added dropwise a solution of 3-chloroperbenzoic acid (77%, 0.57 g, 2.54 mmol) in dichloromethane (5 mL) at 0-5° C. and the mixture was stirred for 5 h. The reaction mixture was washed with saturated sodium bicarbonate solution (2×20 mL) and water (10 mL), and the organic layer was dried over sodium sulfate, filtered and evaporated. The crude product was purified by silica gel column chromatography using dichloromethane:ethyl acetate (5:1→5:2→2:1→1:1) to give the title compound as an off-white solid (0.96 g, 2.25 mmol, 71%). ESMS m/z 426 (M+H)+;

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution (2×20 mL) and water (10 mL)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eb98dc3ca0444ec3b114f9c39b12de38
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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