Sodium hydride → 1-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol

HRID 1845867ノート

反応式

HRID 1845867 の反応式
Cl.[OH:2][CH:3]([CH3:7])[C:4](=[NH:6])[NH2:5].[H-].[Na+].[C:10]([N:12]=[C:13](SC)[S:14][CH3:15])#[N:11]>CN(C)C=O>[NH2:11][C:10]1[N:12]=[C:13]([S:14][CH3:15])[N:5]=[C:4]([CH:3]([OH:2])[CH3:7])[N:6]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 223286992-Hydroxypropanimidamide hydrochloride

生成物 1

HCID 672579331-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol収率 4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

Under a nitrogen atmosphere 2-hydroxypropanimidamide hydrochloride (4.97 g) was suspended in dry N,N-dimethylformamide (25 mL) and sodium hydride (1.66 g, 60 wt % in mineral oil) was added in one portion. When gas evolution ceased the white suspension was heated to 65° C. After 1 h dimethyl cyanocarbonimidodithioate (6.24 g) was added and the mixture was stirred at 65° C. for 18 hours. The reaction mixture was concentrated and triturated with water (200 mL). The resulting precipitate was filtered off, washed with water and the aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL). The combined organic extracts were dried (sodium sulfate) and concentrated before being purified by flash chromatography eluting with 10% methanol in dichloromethane to give the title compound (300 mg) as a yellow oil that solidified on standing.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water (200 mL)
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water
  5. extractionthe aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL)
  6. dry with materialThe combined organic extracts were dried (sodium sulfate)
  7. concentrationconcentrated
  8. custombefore being purified by flash chromatography
  9. washeluting with 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-2bbc8ec5401b4bc1b1c6e6b37d32914b
出典データセット
uspto-grants-2015_02
特許番号
US08952001B2

反応ノート

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