Sodium Carbonate → (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(4-(2-morpholinoethoxy)phenyl)pyrimidin-2-yl)morpholine

HRID 1478563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478563
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:38]2[CH:52]=[CH:51][C:41]([O:42][CH2:43][CH2:44][N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)=[CH:40][CH:39]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:29][N:27]1[CH:28]=[C:24]([C:21]2[N:20]=[C:19]3[N:15]([CH2:14][C@H:10]4[O:11][CH2:12][CH2:13][N:8]([C:5]5[N:4]=[CH:3][C:2]([C:38]6[CH:52]=[CH:51][C:41]([O:42][CH2:43][CH2:44][N:45]7[CH2:46][CH2:47][O:48][CH2:49][CH2:50]7)=[CH:40][CH:39]=6)=[CH:7][N:6]=5)[CH2:9]4)[N:16]=[N:17][C:18]3=[N:23][CH:22]=2)[CH:25]=[N:26]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 46259104-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol esterHCID 73507291HCID 73507291, Verbindung

Produkt 1

HCID 73504500(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(4-(2-morpholinoethoxy)phenyl)pyrimidin-2-yl)morpholineAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

(S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 15 mg (0.03 mmol) was dissolved in dioxane 1 ml, and 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenoxy)ethyl)morpholine 16.5 mg (0.05 mmol), 1M Na2CO3 98 μl (0.09 mmol), and Pd(pph3)4 2 mg (0.001 mmol) were added and then charged with nitrogen, followed by stirring at 105° C. for 18 hours. After the reaction, the reaction mixture was extracted with EA and brine, and the organic layer was dried over MgSO4. Column chromatography (methylene chloride methanol=20:1) gave a product 6 mg (31%).

Aufarbeitung

  1. additioncharged with nitrogen
  2. customAfter the reaction
  3. extractionthe reaction mixture was extracted with EA and brine
  4. dry with materialthe organic layer was dried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-68da80ab8f1f48d2af68abab842855ed
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403831B2

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