Acetic Acid → 2-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

HRID 19666

반응식

HRID 19666 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1.C(O)(=O)C>O1CCOCC1.O>[CH3:19][S:18][C:14]1[N:15]=[C:16]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:12][N:13]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidine

생성물 1

HCID 111838682-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

Benzyl alcohol (1.3 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 0.74 g) in 12.4 mL of dry dioxane, and the mixture was stirred at 100° C. for 30 min. A solution of 4-chloro-2-(methylthio)pyrimidine (2.0 g) in dry dioxane (8.2 mL) was added dropwise at 50° C. and the mixture was stirred at this temperature for 5 hours. After cooling at room temperature the mixture was acidified with glacial acetic acid, treated with water and extracted with dichloromethane. The organic phases were dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (70 g) eluting with ciclohexane/ethyl acetate from 95/5 to 9/1 to give the title compound as a white solid (1.22 g).

후처리

  1. stirringthe mixture was stirred at this temperature for 5 hours
  2. temperatureAfter cooling at room temperature the mixture
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by a silica SPE cartridge (70 g)
  8. washeluting with ciclohexane/ethyl acetate from 95/5 to 9/1

출처 및 근거

ORD 기록
ord-cf272e86264b42c7abe6ebbb6c17ca0d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745458B2

연결된 노트

불러오는 중…