Ethylene Glycol → HCID 118205820, compound

HRID 521676Notes

Reaction equation

[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12](NNS(C2C=CC(C)=CC=2)(=O)=O)[C:13]2[N:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=2[N:15]=1)[CH3:2].C(O)CO.[OH-].[Na+]>O>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[CH:12][C:13]2[N:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][C:14]=2[N:15]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 156 mg of 1-[2-(2-ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidin-4-yl]-2-tosylhydrazine and 12 ml of ethylene glycol was added to a mixture of 4 ml of an 8% aqueous sodium hydroxide solution and 2 ml of ethylene glycol at 80° C., and the mixture was stirred at 100° C. for 40 minutes. Water was added to the cooled reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 40 mg of 2-(2-ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidine (Compound of Present Invention 18).

Workup

extractionthe mixture was extracted with t-butyl methyl ether
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-d3e94638df1f4ff9a75621307fcb98e4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328121B1

Reaction notes

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