Potassium Carbonate → 2-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidine

HRID 2175244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175244
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15](=O)([O-])[O-].[K+].[K+].BrC[C:23]1[CH:24]=[N:25][C:26]([S:29][CH3:30])=[N:27][CH:28]=1>CN(C=O)C.CCOC(C)=O>[CH3:30][S:29][C:26]1[N:25]=[C:24]([CH2:15][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH:23]=[CH:28][N:27]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 60209911HCID 60209911, Verbindung

Produkt 1

HCID 709823642-(Methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol), potassium carbonate (0.356 g, 2.58 mmol) and 5-(bromomethyl)-2-(methylthio)pyrimidine (30% in THF, 2.070 g, 2.83 mmol) in DMF (5 mL) was stirred at room temperature for 14 h. After this time, the reaction mixture was diluted with EtOAc, washed with saturated sodium bicarbonate, dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.6 g, 70% yield) as a light yellow solid. LCMS, [M+H]+=333.2. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=5.1 Hz, 1H), 7.87 (s, 1H), 7.81 (s, 1H), 6.49 (d, J=5.1 Hz, 1H), 5.36 (s, 2H), 2.56 (s, 3H), 1.33 (s, 12H).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b1135a91db0e49a8857af47de88e6a68
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062028B2

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