Triethylamine → 5-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine

HRID 531226노트

반응식

HRID 531226 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[C:8]([CH2:15]O)=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1.CCN(CC)CC>C(Cl)Cl>[Br:6][C:7]1[C:8]([CH2:15][S:2]([CH3:1])(=[O:4])=[O:3])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66524860(5-Bromo-2-(methylthio)pyrimidin-4-yl)methanol2회

생성물 1

HCID 772307075-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Methanesulfonyl chloride (5.85 g, 51.0 mmol) was added to a stirred, cooled 0° C. mixture of [5-bromo-2-(methylthio)pyrimidin-4-yl]methanol (INTERMEDIATE 1, 10 g, 42.5 mmol) in CH2Cl2 (200 mL), followed by addition of Et3N (6.46 g, 63.8 mmol). The mixture was stirred at 0° C. for 30 minutes. TLC showed no starting material left. The mixture was quenched with water (30 mL) and the mixture was washed with more water (50 mL). The organic portion was washed with brine (saturated, 50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, eluting with EtOAc/hexane (3/7) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 8.61 (s, 1H), 5.38 (s, 2H), 3.21 (s, 3H), 2.60 (s, 3H).

후처리

  1. waitleft
  2. customThe mixture was quenched with water (30 mL)
  3. washthe mixture was washed with more water (50 mL)
  4. washThe organic portion was washed with brine (saturated, 50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with EtOAc/hexane (3/7)

출처 및 근거

ORD 기록
ord-9523fc0df1404210b9ebefe97b8a30bf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353101B2

반응 노트

불러오는 중…