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

HRID 1845867노트

반응식

HRID 1845867 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2bbc8ec5401b4bc1b1c6e6b37d32914b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952001B2

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