Ammonium Chloride → HCID 68687425, compound

HRID 2238685Notes

Reaction equation

HRID 2238685 reaction equation
[C:1]([C:4]1[C:5]2[N:6]([C:10]([C:13]3[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]([S:21][CH3:22])[N:14]=3)=[CH:11][N:12]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:23][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[OH:3][C:1]([C:4]1[C:5]2[N:6]([C:10]([C:13]3[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]([S:21][CH3:22])[N:14]=3)=[CH:11][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:23])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 68689643HCID 68689643, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 68687425HCID 68687425, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of the 4-(8-acetylimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [156-1] was dissolved in 5 mL of tetrahydrofuran, then 577 μL of methylmagnesium bromide (0.84M tetrahydrofuran solution) was added in an ice-cold condition, and stirred overnight at room temperature. 200 μL of methylmagnesium bromide was further added and stirred at room temperature for 4 hours, then a saturated aqueous solution of ammonium chloride was added to terminate the reaction. The reaction solution was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 18 mg of 4-[8-(1-hydroxy-1-methylethyl)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [157-1] as a brown solid.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. customto terminate
  3. customthe reaction
  4. extractionThe reaction solution was extracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe thus obtained residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-ab32e900231c463c93d15578dab775de
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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