m-Chloroperbenzoic acid → HCID 11951347, compound

HRID 1454445Notes

Reaction equation

HRID 1454445 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>ClCCl>[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=3)[C:4]=2[N:5]=[C:6]([S:8]([CH3:9])=[O:33])[N:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11530828HCID 11530828, compound

Product 1

HCID 11951347HCID 11951347, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-Chloro-2-methylsulfanyl-8-(4-trifluoromethyl-phenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (1.0 g, 2.7 mmol) in dichloromethane (50 mL) was mixed with m-CPBA (0.63 g, 4.0 mmol). The resultant mixture was stirred at room temperature for 10 minutes and concentrated under vacuum. Flash chromatography (EtOAc/Hexane, 3:1) then provided the title compound (0.86 g, 82%): MS (ES) m/z 388 (M+H)+; 1H-NMR(CDCl3) δ 2.80 (s, 3H), 7.03 (d, J=9.9 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 2H), 8.19 (d, J=9.9 Hz, 1H).

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-79b33b3b12d748d9942f8e7416ff2d85
Source dataset
uspto-grants-2009_01
Patent number
US07479558B2

Reaction notes

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