Water → cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyrazinyl]morpholine

HRID 2278419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278419
CC1(C)C(C)(C)OB([C:9]2[CH:13]=[CH:12][O:11][C:10]=2[CH3:14])O1.Cl[C:17]1[N:22]=[C:21]([N:23]2[CH2:28][C@H:27]([CH3:29])[O:26][C@H:25]([CH3:30])[CH2:24]2)[CH:20]=[N:19][CH:18]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:30][C@H:25]1[O:26][C@@H:27]([CH3:29])[CH2:28][N:23]([C:21]2[CH:20]=[N:19][CH:18]=[C:17]([C:9]3[CH:13]=[CH:12][O:11][C:10]=3[CH3:14])[N:22]=2)[CH2:24]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 242295474,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolaneHCID 86702421cis-4-(6-Chloro-2-pyrazinyl)-2,6-dimethylmorpholine

Produkt 1

HCID 67513262cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyrazinyl]morpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4,4,5,5-Tetramethyl-2-(2-methyl-3-furanyl)-1,3,2-dioxaborolane (567 mg, 2.72 mmol) was added to a solution of cis-4-(6-chloro-2-pyrazinyl)-2,6-dimethylmorpholine (620 mg, 2.72 mmol) in a mixture of 1,4-dioxane (17 mL), water (2.83 mL) and sodium carbonate (577 mg, 5.45 mmol). The solution was degassed using argon gas and then charged with tetrakis(triphenylphosphine)palladium(0) (315 mg, 0.272 mmol). After addition, the reaction mixture was stirred and heated in the microwave at 100° C. for 1 hour. Crude LCMS shows desired product and starting material so the reaction mixture was stirred and heated for a further 1 hour at 100° C. in the microwave. Crude LCMS shows desired product and no starting material can be seen. The reaction mixture washed with ethyl acetate (200 mL), water (100 mL), filtered and then evaporated to dryness. The residue was dissolved in dichloromethane (˜5 ml) and purified on silica by a Biotage SP4 chromatographic system (40+M cartridge, eluted with 0-50% ethyl acetate in isohexanes). Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound (441 mg, 1.533 mmol, 56.3% yield). LC/MS [M+H]+=274.

Aufarbeitung

  1. customThe solution was degassed
  2. additionAfter addition

Quellen und Nachweise

ORD-Eintrag
ord-034b285680af4b9ba3965068025f0d70
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133178B2

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