Sodium Carbonate → HCID 86673495, Verbindung

HRID 629008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629008
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:16])[N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=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>[Cl:16][C:4]1[C:5]([S:14][CH3:15])=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=[C:2]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[N:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 866734944-(2,6-Dichloro-5-methylsulfanyl-pyrimidin-4-yl)-morpholine

Produkt 1

HCID 86673495HCID 86673495, Verbindung

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, 0.71 mmol.), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-aniline) (172.0 mg, 0.781 mmol.), (PPh3)4Pd (437 mg, 0.07 mmol.), 2M Na2CO3 (1.0 ml, 2.13 mmol, 3.0 eq.) and dioxane (15.0 ml) was added to the reaction vessel which was flushed with argon. The reaction mixture was stirred at 90° C. for 12 hrs and then dried so that the solvent was evaporated. The reaction mixture was partitioned between EA and water. The organic layers were collected, washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 3:2) to give a pale yellow solid of 102 mg (42.3%).

Aufarbeitung

  1. additionwas added to the reaction vessel which
  2. customwas flushed with argon
  3. customdried so that the solvent
  4. customwas evaporated
  5. customThe reaction mixture was partitioned between EA and water
  6. customThe organic layers were collected
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 3:2)
  12. customto give a pale yellow solid of 102 mg (42.3%)

Quellen und Nachweise

ORD-Eintrag
ord-70ff08af05a84a7eba217148d7346044
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315491B2

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