Potassium Carbonate → 4-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamide

HRID 452042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452042
[CH3:1][NH:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[CH3:19].Br[C:22]1[N:27]=[N:26][C:25]([NH2:28])=[N:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.CO.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>[NH2:28][C:25]1[N:26]=[N:27][C:22]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:20])=[C:5]([CH3:19])[CH:6]=2)=[CH:23][N:24]=1

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 153325646-Bromo-1,2,4-triazin-3-amineHCID 57516536N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Produkt 1

HCID 575165354-(3-amino-1,2,4-triazin-6-yl)-N,2-dimethylbenzamideAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Step 2, 0.3 g, 0.001 mol), 6-bromo-1,2,4-triazin-3-amine (0.21 g, 1.2 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol) and potassium carbonate (0.45 g, 3.3 mmol) in toluene (1.9 mL), ethanol (0.94 mL) and water (0.94 mL). The resulting mixture was heated at 130° C. for 2.5 h. The mixture was diluted with MeOH, filtered, and washed with DCM/methanol (90%). The filtrate was concentrated. The residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM to afford the desired product (110 mg, 41%). LCMS (M+H)+: m/z=244.3.

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with DCM/methanol (90%)
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by flash chromatography on a silica gel column with 10% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-abc0bf1818d4434e95d3f929d6adc733
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487096B2

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