Potassium Carbonate → 5-(5-Iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamine

HRID 38388

Reaktionsgleichung

Reaktionsgleichung von HRID 38388
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:13]([OH:19])=[C:12]([I:20])[CH:11]=2)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Cl)[C:28]#[CH:29]>CN(C)C=O>[I:20][C:12]1[C:13]([O:19][CH2:29][C:28]#[CH:27])=[CH:14][C:15]([CH:16]([CH3:18])[CH3:17])=[C:10]([CH:11]=1)[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 159538644-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol

Produkt 1

HCID 595987185-(5-Iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamineAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol (200 mg, 0.43 mmol) dissolved in anhydrous N,N-dimethylformamide (2 mL) was added anhydrous potassium carbonate (414 mg, 3.00 mmol) and propargyl chloride (0.03 mL, 0.43 mmol). After stirring at room temperature overnight, the reaction was extracted with dichloromethane, water and brine. The dichloromethane layer was dried using anhydrous magnesium sulfate, concentrated, and purified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide) to yield 5-(5-iodo-2-isopropyl-4-prop-2-ynyloxy-phenoxy)-pyrimidine-2,4-diamine as white solid (131 mg, 71%), MS (M+H)=425.

Aufarbeitung

  1. extractionthe reaction was extracted with dichloromethane, water and brine
  2. dry with materialThe dichloromethane layer was dried
  3. concentrationconcentrated
  4. custompurified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-083b306a62864c61b65dfa1b32c2e254
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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