m-Chloroperbenzoic acid → HCID 57530505, compound

HRID 1454468Notes

Reaction equation

HRID 1454468 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[C:11](=[O:14])[NH:12][CH2:13][C:3]=12.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([S:8]([CH3:9])=[O:31])[N:5]=[C:4]2[N:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[C:11](=[O:14])[NH:12][CH2:13][C:3]=12

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 575305005-Chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 57530505HCID 57530505, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.71 g, 5 mmol) in CH2Cl2 (60 mL) was added m-CPBA (1.17 g, 5.2 mmol). The mixture was stirred at room temperature for 10 minutes, then directly loaded onto a column. Flash chromatography (mobile phase EtOAc/Hexane) afforded the title compound as a white solid 1.58 g (88%). LC-MS m/z 358 (M+H)+.

Sources & evidence

ORD record
ord-655085dc99dd4164a114fce435f6f46b
Source dataset
uspto-grants-2009_01
Patent number
US07479558B2

Reaction notes

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