Sodium Carbonate → 2-(5-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine

HRID 1621410

Reaktionsgleichung

O1CCOCC1.[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[CH:13]=[C:14](B(O)O)[C:15]([F:18])=[N:16][CH:17]=1.Cl[C:23]1[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([S:30][CH3:31])[N:24]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O>[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C:12]1[CH:13]=[C:14]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([S:30][CH3:31])[N:24]=2)[C:15]([F:18])=[N:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

1,4-Dioxane (16 mL) and water (3.3 mL) were added to a mixture of 5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid (0.715 g, 3.53 mmol), 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (0.682 g, 3.88 mmol), Pd(PPh3)4 (0.408 g, 0.353 mmol), and Na2CO3 (0.935 g, 8.82 mmol) and the suspension was heated at 90° C. for 2 h. After cooling, the mixture was filtered, washed with EtOAc (2×20 mL), and the combined organic phases were concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (hexanes to 30% ethyl acetate in hexanes) to give 2-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine (0.5259 g, 1.706 mmol, 48.3% yield) as a white solid. LCMS (API-ES) m/z 309 (M+H)+.

Aufarbeitung

temperatureAfter cooling
filtrationthe mixture was filtered
washwashed with EtOAc (2×20 mL)
concentrationthe combined organic phases were concentrated
customchromatographed through a Redi-Sep pre-packed silica gel column (hexanes to 30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-8a82a85e99b54ca7a7360330eed5d9e2
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08772480B2

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