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Lithium Chloride → HCID 71240815, Verbindung

HRID 1774607
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1774607
C[Sn](C)(C)[Sn](C)(C)C.[Cl-].[Li+].Cl[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([Cl:28])[CH:19]=2)[N:15]=[CH:14][N:13]=1.[CH3:29][O:30][C:31]([CH:33]1[CH2:37][C:36](OS(C(F)(F)F)(=O)=O)=[CH:35][N:34]1[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:32]>C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:29][O:30][C:31]([CH:33]1[CH2:37][C:36]([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([Cl:28])[CH:19]=3)[N:15]=[CH:14][N:13]=2)=[CH:35][N:34]1[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 433294Lithium ChlorideHCID 85161366HCID 85161366, VerbindungHCID 89396901HCID 89396901, VerbindungHCID 178477788HCID 178477788, Verbindung

Produkt 1

HCID 71240815HCID 71240815, VerbindungAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hexamethyldistannane (5.6 ml, 2.7 mmol) and lithium chloride (0.34 g, 7.8 mmol) were added sequentially in one portion to a stirred solution of, 4-chloro-6-(3-chloro-4-isopropoxy-phenyl)-pyrimidine (0.75 g, 2.7 mmol) and 4-trifluoromethanesulfonyloxy-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.0 g, 2.7 mmol) in THF (40 ml). The mixture was degassed with nitrogen for 5 minutes, after which time palladium tetrakis(triphenylphosphine) (0.31 g, 0.26 mmol) was added in one portion, the mixture was then heated to 70° C. and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (200 ml) and saturated potassium fluoride (50 ml). The organic layer was separated, washed sequentially with water (100 ml) then brine (100 ml) before being dried (MgSO4), filtered and concentrated. The resulting red gum was purified by flash column chromatography (elution: 80% EtOAc, 20% Heptane) to give the title compound (0.1 g, 9% yield) as a colourless oil. Tr=2.69 min m/z (ES+) (M+H+) 474.

Aufarbeitung

  1. customThe mixture was degassed with nitrogen for 5 minutes
  2. temperatureAfter this time the reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate (200 ml) and saturated potassium fluoride (50 ml)
  4. customThe organic layer was separated
  5. washwashed sequentially with water (100 ml)
  6. dry with materialbrine (100 ml) before being dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting red gum was purified by flash column chromatography (elution: 80% EtOAc, 20% Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-bda38543c00c42d784b7db45bbb755c1
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09260422B2

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