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Triethylamine → HCID 178478262, Verbindung

HRID 541849
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 541849
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6](/[CH:10]=[CH:11]\[C:12]2[CH:13]=[C:14]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[C:21](Cl)[N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH:5]=1.C(N(CC)CC)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:25][C:24]1[CH:23]=[N:22][C:21]2[NH:3][C:4]3[CH:9]=[CH:8][N:7]=[C:6]([CH:5]=3)[CH:10]=[CH:11][C:12]3[CH:13]=[C:14]([NH:18][C:19]=1[N:20]=2)[CH:15]=[CH:16][CH:17]=3
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86636271N-{3-[(Z)-2-(4-Aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine Dihydrochloride

Produkt 1

HCID 178478262HCID 178478262, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of N-{3-[(Z)-2-(4-aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine dihydrochloride (34.6 mg, 0.08 mmol) and triethylamine (0.034 mL, 0.24 mmol) in dry 1,4-dioxane (0.70 mL) was added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.8 mg, 0.0048 mmol), palladium acetate (0.7 mg, 0.003 mmol) and cesium carbonate (52.3 mg, 0.16 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 150° C. for 30 min. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give the residue, which was then triturated with MeOH/EtOAc/THF to provide the desired product as a light yellow powder (9 mg, 35%). LCMS for C17H13ClN5 (M+H)+: m/z=322.0. 1H NMR (300 MHz, DMSO-d6): δ 9.81 (s, 1H), 9.33 (s, 1H), 9.15 (s, 1H), 8.49 (s, 1H), 8.26 (m, 1H), 8.19 (s, 1H), 7.33 (m, 1H), 7.24 (m, 1H), 7.08 (d, J=5.7 Hz, 1H), 6.93 (dd, J=5.7, 2.1 Hz, 1H), 6.83 (m, 1H), 6.58 (d, J=13.5 Hz, 1H).

Aufarbeitung

  1. customThe mixture was degassed
  2. customby bubbling N2 through the solution
  3. customThe sealed tube was then microwaved at 150° C. for 30 min
  4. additionThe reaction mixture was diluted with THF/MeOH
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the residue, which
  8. customwas then triturated with MeOH/EtOAc/THF

Quellen und Nachweise

ORD-Eintrag
ord-2be50dd881c74e9693c1ea7436fd77ab
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871753B2

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