Potassium Phosphate, Tribasic → 2-(4-Methoxy-2,6-dimethylphenyl)-5-morpholinopyridin-3-amine

HRID 1431587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431587
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20](B(O)O)=[C:19]([CH3:27])[CH:18]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([C:2]2[C:7]([NH2:8])=[CH:6][C:5]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][N:3]=2)=[C:19]([CH3:27])[CH:18]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 3716303(2,6-Dimethyl-4-methoxyphenyl)boronic acidHCID 596310392-Chloro-5-morpholinopyridin-3-amine

Produkt 1

HCID 596311642-(4-Methoxy-2,6-dimethylphenyl)-5-morpholinopyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Chloro-5-morpholinopyridin-3-amine (62 mg, 0.29 mmol), 4-methoxy-2,6-dimethylphenylboronic acid (0.07 g, 0.39 mmol), tricyclohexylphosphine (12 mg, 0.042 mmol), and tris(dibenzylideneacetone)dipalladium (0) (19 mg, 0.02 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (3 mL) and aq. 1.3M potassium phosphate tribasic (0.67 mL, 0.87 mmol) were added by syringe. The resulting reaction was heated to 90° C. and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-30% of a premixed solution of 89:9:1 DCM:MeOH:ammonium hydroxide in DCM) to afford a light yellow solid as 2-(4-methoxy-2,6-dimethylphenyl)-5-morpholinopyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 7.75 (1H, br. s.), 6.75 (3H, m), 3.95 (4H, m), 3.85 (3H, m), 3.54 (2H, br. s.), 3.28 (4H, m), 2.04 (6H, s). Mass Spectrum (pos.) m/e: 314.2 (M+1).

Aufarbeitung

  1. customthen degassed
  2. customThe resulting reaction
  3. temperaturethe reaction was cooled to rt
  4. extractionAfter extracting twice with EtOAc and twice with DCM
  5. extractionthe combined organic extractions
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified on silica gel (0-30% of a premixed solution of 89:9:1 DCM:MeOH:ammonium hydroxide in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-08305a0d110c4588a5c3ba8bf9ba8859
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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