4-Chloro-5-iodo-2-(methylthio)pyrimidine → (4-Chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol

HRID 38329노트

반응식

HRID 38329 반응식
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1.C([Mg]Br)(C)C.[CH:16]([C:19]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=1[CH:21]=[O:22])([CH3:18])[CH3:17]>C1COCC1>[Cl:1][C:2]1[C:7]([CH:21]([C:20]2[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:19]=2[CH:16]([CH3:18])[CH3:17])[OH:22])=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1

참가 물질

5

반응물 3

HCID 136365194-Chloro-5-iodo-2-(methylthio)pyrimidineHCID 541451142-Isopropyl-4,5-dimethoxy-benzaldehydeHCID 178418365HCID 178418365, 화합물

생성물 1

HCID 59598617(4-Chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-chloro-5-iodo-2-methylsulfanyl-pyrimidine (1.10 g, 3.9 mmol) in 20 mL THF at −40° C. was added isopropyl magnesium bromide (2.3 mL, 2 M in THF)) over 5 minutes. After 30 minutes, 2-isopropyl-4,5-dimethoxy-benzaldehyde from step 3 (1.04 g, 4.6 mmol) was added and the solution was warmed to room temperature. The mixture was quenched by the addition of brine, and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (ethyl acetate) afforded (4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol (1.168 g, 82%) as a light yellow solid.

후처리

  1. customThe mixture was quenched by the addition of brine
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-50d76addffd549c580e4714bf8ebf9d3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524725B2

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