Triethylamine → HCID 178461601, Verbindung

HRID 522809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522809
Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:7]=[C:6]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]1[CH3:24])[N:5]=2.[NH:25]1[CH:29]=[CH:28][C:27](B(O)O)=[N:26]1.CCN(CC)CC>C(COC)OC.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:24][C@H:19]1[CH2:20][O:21][CH2:22][CH2:23][N:18]1[C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([C:29]3[CH:28]=[CH:27][NH:26][N:25]=3)[NH:3]2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:7]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 178461599HCID 178461599, VerbindungHCID 178514837HCID 178514837, Verbindung

Produkt 1

HCID 178461601HCID 178461601, VerbindungAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

8-Bromo-2-((S)-3-methyl-morpholin-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (50 mg, 126 μmol) was dissolved in dimethoxyethane (2 mL) and water (0.2 mL), followed by addition of 1H-pyrazole-3-ylboronic acid (21.1 mg, 189 μmol), PdCl2(dppf) (9.21 mg, 13 μmol) and NEt3 (53 μl, 378 μmol) under argon. The reaction mixture was heated to 85° C. for 23 hours. The reaction mixture was then diluted with EtOAc, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (12 g SiO2, EtOAc) to give the product (19 mg, 39% yield).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (12 g SiO2, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8445d1de8ad647769629ef46a8d250aa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334271B2

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