Hydrogen Peroxide → 2-(Tert-butylamino)-4-(methylthio)pyrimidine-5-carboxamide

HRID 2280763Notes

Reaction equation

[C:1]([NH:5][C:6]1[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]#[N:15])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:16].[Na+].OO.O>CS(C)=O>[C:1]([NH:5][C:6]1[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]([NH2:15])=[O:16])=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 2-(tert-butylamino)-4-(methylthio)pyrimidine-5-carbonitrile (0.6 g, 2.70 mmol) in DMSO (7 mL) was added 6M aqueous sodium hydroxide solution (2.249 mL, 13.49 mmol) and 30% aqueous hydrogen peroxide (1.530 mL, 13.49 mmol) solution at 0° C. Then the mixture was stirred at 50° C. for 15 min. The reaction mixture was poured into water (40 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration of the filtrate under reduced pressure gave the crude product, which was purified by silica gel column chromatography (5% methanol in DCM) to afford 2-(tert-butylamino)-4-(methylthio)pyrimidine-5-carboxamide (0.462 g, 1.922 mmol, 71.2% yield) as a white solid. MS (ESI) m/z 241.0 [M+1]+.

Workup

extractionextracted with ethyl acetate (3×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customConcentration of the filtrate under reduced pressure gave the crude product, which
customwas purified by silica gel column chromatography (5% methanol in DCM)

Sources & evidence

ORD record: ord-bbbf147825b047b9bbbeb2b97b0c6ad7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

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