Sodium methanethiolate → (5-Methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester

HRID 719919ノート

反応式

HRID 719919 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14]Br)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][S-:18].[Na+]>CC(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][S:18][CH3:17])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 4378561Sodium methanethiolateHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

生成物 1

HCID 67482522(5-Methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
25 °C

実験手順

A solution of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (prepared according to WO 02/070494, 1.03 g, 3.575 mmol) in acetone (11.6 mL) was treated with sodium thiomethoxide (0.33 g, 4.473 mmol). The reaction mixture was stirred at 25° C. for 5 h 15 min. The reaction was then concentrated in vacuo, and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The aqueous layer was back-extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 5% ethyl acetate/methylene chloride) afforded (5-methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester as a crude white solid (0.45 g, 49%) which was used without further purification.

後処理

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. extractionThe aqueous layer was back-extracted with ethyl acetate (100 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-88bd57ef58ec4f9ba95c336acb1792e7
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

反応ノート

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