Potassium Carbonate → 4-[8-(Difluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile

HRID 2238689Notes

Reaction equation

[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]([F:33])([F:32])C([O-])=O.[Na+]>C(#N)C.C(Cl)(Cl)Cl>[F:32][CH:28]([F:33])[O:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

20 mg of the 4-(8-hydroxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [158-1] was dissolved in 1 mL of acetonitrile, then 20 mg of potassium carbonate and 13 mg of sodium chlorodifluoroacetate were added, and stirred overnight at 90° C. After cooling the reaction mixture back to room temperature, diluted in 100 mL of chloroform, and washed with water and dried over anhydrous magnesium sulfate. The insolubles were filtered, then the filtrate was concentrated under reduced pressure and purified by preparative thin-layer chromatography, to obtain 15 mg of 4-[8-(difluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [161-1] as a light brown solid.

Workup

temperatureAfter cooling the reaction mixture back to room temperature
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationThe insolubles were filtered
concentrationthe filtrate was concentrated under reduced pressure
custompurified by preparative thin-layer chromatography

Sources & evidence

ORD record: ord-f1a20971fa71487abda4ed54319cbc1c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718801B2

Reaction notes

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