Iodoethane → 5-[5-(Ethylsulfonyl)-4-methoxy-2-(1-methylethyl)phenoxy]-2,4-pyrimidinediamine

HRID 38393노트

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HRID 38393 반응식
S([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([O:15][C:16]2[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:18][C:19]([O:26][CH3:27])=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:21]=2)=[CH:10][N:9]=1.C(=O)(O)[O-].[Na+].[CH2:36](I)[CH3:37]>O.O1CCOCC1>[CH2:36]([S:22]([C:20]1[C:19]([O:26][CH3:27])=[CH:18][C:17]([CH:28]([CH3:30])[CH3:29])=[C:16]([CH:21]=1)[O:15][C:11]1[C:12]([NH2:14])=[N:13][C:8]([NH2:7])=[N:9][CH:10]=1)(=[O:24])=[O:23])[CH3:37]

참가 물질

7

반응물 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 59598561HCID 59598561, 화합물

생성물 1

HCID 573292025-[5-(Ethylsulfonyl)-4-methoxy-2-(1-methylethyl)phenoxy]-2,4-pyrimidinediamine수율 20%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of sodium sulfite (541 mg, 4.29 mmol) in water (20 mL) was added 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzenesulfonyl chloride (400 mg, 1.07 mmol) and the reaction was heated at 80° C. for 1 hour. Sodium bicarbonate (361 mg, 4.29 mmol-dissolved in 5 mL water), dioxane (20 mL), and ethyl iodide (0.10 mL, 1.29 mmol) were added and the reaction was heated at 80° C. for 2 hours. The reaction was concentrated, extracted with dichoromethane (150 mL) and water (20 mL). The dichloromethane layer was dried using anhydrous sodium sulfate, concentrated, and purified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide) to yield 5-(5-ethanesulfonyl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (77 mg, 20%) as white solid, MS (M+H)=367.

후처리

  1. temperaturethe reaction was heated at 80° C. for 2 hours
  2. concentrationThe reaction was concentrated
  3. extractionextracted with dichoromethane (150 mL) and water (20 mL)
  4. dry with materialThe dichloromethane layer was dried
  5. concentrationconcentrated
  6. custompurified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide)

출처 및 근거

ORD 기록
ord-92d6e37bfbc849b49b2abd063f2362bb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524725B2

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