Potassium Carbonate → 5-(3-amino-1,2,4-triazin-6-yl)-N-methylpyridine-2-carboxamide
Reaktionsgleichung
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][N:6]=1)=[O:4].Br[C:21]1[N:26]=[N:25][C:24]([NH2:27])=[N:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.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>[NH2:27][C:24]1[N:25]=[N:26][C:21]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][CH:7]=2)=[CH:22][N:23]=1Komponenten
8
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 4
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A mixture of N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (200 mg, 0.80 mmol) (VWR, Cat. #200068-640), 6-bromo-1,2,4-triazin-3-amine (130 mg, 0.76 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.04 mmol) and potassium carbonate (0.32 g, 2.3 mmol) in toluene (1.3 mL), ethanol (0.66 mL) and water (0.66 mL) was heated at 120° C. for 1.5 h. The mixture was filtered and washed with methanol. The filtrate was purified by RP-HPLC (pH=10) to afford the desired product (80 mg, 45.54%). LCMS (M+H)+: m/z=231.4; LCMS (M+H+H2O)+: m/z=249.3.
Aufarbeitung
- filtrationThe mixture was filtered
- washwashed with methanol
- customThe filtrate was purified by RP-HPLC (pH=10)
Quellen und Nachweise
- ORD-Eintrag
- ord-cdfea299194a47c8a3cf4c4c6abf11f3
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09221824B2
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