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

HRID 925178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925178
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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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 dichloromethane (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.

Aufarbeitung

  1. temperaturethe reaction was heated at 80° C. for 2 hours
  2. concentrationThe reaction was concentrated
  3. extractionextracted with dichloromethane (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)

Quellen und Nachweise

ORD-Eintrag
ord-3583ad591af74304b751ce92ffbf810e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284279B2

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