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

HRID 2238689ノート

反応式

HRID 2238689 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 68690427HCID 68690427、化合物

生成物 1

HCID 686862754-[8-(Difluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile収率 63.7%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f1a20971fa71487abda4ed54319cbc1c
出典データセット
uspto-grants-2010_05
特許番号
US07718801B2

反応ノート

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