m-Chloroperbenzoic acid → 6-bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1190932Notes

Reaction equation

[Br:1][C:2]1[C:13](=[O:14])[N:12]([CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH:23]2[CH2:25][CH2:24]2)[C:5]2[N:6]=[C:7]([S:10][CH3:11])[N:8]=[CH:9][C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[Br:1][C:2]1[C:13](=[O:14])[N:12]([CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH:23]2[CH2:25][CH2:24]2)[C:5]2[N:6]=[C:7]([S:10]([CH3:11])=[O:34])[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of 6-bromo-8-(2-cyclopropyl-6-fluorobenzyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (8, 500 mg, 1.2 mmol) in dichloromethane (20 mL) was added 3-chloroperbenzoic acid (77%, 253 mg, 1.1 mmol) in dichloromethane (15 mL) at 0-5° C. and the mixture was stirred at 0-5° C. for 1 h. The reaction mixture was washed with saturated sodium bicarbonate solution (2×30 mL) then with brine (30 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography eluting with chloroform to yield the title compound as a white solid (385 mg, 0.9 mmol, 74%). ESMS m/z 436 (M+H)+.

Workup

washThe reaction mixture was washed with saturated sodium bicarbonate solution (2×30 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified by column chromatography
washeluting with chloroform

Sources & evidence

ORD record: ord-8b9744ff3b074ca2ab0c31c5edf54225
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680099B2

Reaction notes

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