Sodium Carbonate → HCID 53329145, Verbindung

HRID 629038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629038
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([S:14][CH3:15])=[C:4](Cl)[N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)O1.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.O1CCOCC1>[CH3:15][S:14][C:5]1[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:7][C:2]([C:29]2[CH:28]=[N:27][CH:26]=[CH:25][CH:30]=2)=[N:3][C:4]=1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 866734944-(2,6-Dichloro-5-methylsulfanyl-pyrimidin-4-yl)-morpholine

Produkt 1

HCID 53329145HCID 53329145, VerbindungAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-(2,6-dichloro-5-methylsulfanyl-pyrimidin-4-yl)-morpholine (200 mg, 0.717 mmol.), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (323 mg, 1.577 mmol, 2.2 eq), (PPh3)4Pd (165 mg, 0.2 mmol.), 2M Na2CO3 (2.1 ml, 4.302 mmol, 6.0 eq.) and dioxane (20 ml) was added to a reaction vessel which was then flushed with argon. The reaction mixture was stirred at 90° C. for 16 hrs, and then dried. The solvent was removed by evaporation. The mixture was partitioned between EA and water. The organic layer was collected, washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified using flash chromatography on silica gel (Hexane/EtOAc 2:3, few Et3N), recrystallized by (Hexane/EtOAc) to give a pale yellow solid 57.8 mg (22.1%).

Aufarbeitung

  1. additionwas added to a reaction vessel which
  2. customwas then flushed with argon
  3. customdried
  4. customThe solvent was removed by evaporation
  5. customThe mixture was partitioned between EA and water
  6. customThe organic layer was collected
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe resulting residue was purified
  12. customrecrystallized by (Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4cc1a2e71a2d4b1983a48b46c523532c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315491B2

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