Hydrogen Peroxide → HCID 71612266, compound

HRID 1484697Notes

Reaction equation

HRID 1484697 reaction equation
[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:34][CH2:35][CH2:36][S:37]([CH3:39])=[O:38])=[CH:23][N:22]=3)[C:5]=2[CH3:40])[CH2:3][CH2:2]1.OO.N(C(OCC)=O)=NC(OCC)=[O:46]>O1CCCC1>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:11]([F:20])=[CH:12][C:13]([O:17][CH2:18][CH3:19])=[CH:14][C:15]=3[F:16])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:34][CH2:35][CH2:36][S:37]([CH3:39])(=[O:46])=[O:38])=[CH:23][N:22]=3)[C:5]=2[CH3:40])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 71612145HCID 71612145, compound

Product 1

HCID 71612266HCID 71612266, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

100 mg of 2-[5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-5-[2-(methylsulfinyl)ethoxy]-N-(pyridin-4-yl)pyrimidin-4-amine (2-8-1, 0.176 mmol, 1.0 eq.) were suspended in 0.93 mL dry tetrahydrofuran under a nitrogen atmosphere. 90 μL hydrogen peroxide (30%, 0.879 mmol, 5.0 eq.) and 33 μL diethyl azodicarboxylate (0.211 mmol, 1.2 eq.) were added. The reaction mixture was stirred at 50° C. for 2 hours and concentrated in vacuo. The crude product was purified by flashcromatography to provide 31.9 mg (0.05 mmol, 31%) of the analytically pure target compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by flashcromatography
  3. customto provide 31.9 mg (0.05 mmol, 31%) of the analytically pure target compound

Sources & evidence

ORD record
ord-eda91c3b3f194734bf456ad2fe8262fe
Source dataset
uspto-grants-2016_08
Patent number
US09422268B2

Reaction notes

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