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Dimethylformamide → HCID 11749692, Verbindung

HRID 2216312
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216312
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH3:40][N:41](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:40]#[N:41])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 86595018HCID 86595018, Verbindung

Produkt 1

HCID 11749692HCID 11749692, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (146 mg, 0.283 mmol), zinc cyanide (66 mg, 0.57 mmol), and DMF (2 mL) was degassed with N2 for 10 min, and then Pd(PPh3)4 (16 mg, 0.014 mmol) was added. The mixture was stirred at 80° C. under N2 for 2 h and then cooled to room temperature. The reaction mixture was treated with saturated aqueous NaHCO3, and extracted (3×) with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide the target compound (108 mg, 97%) as a white solid: mp 258–260° C.; 1H NMR (500 MHz, CDCl3) δ 8.76 (s, 1H), 8.21 (br s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.84 (d, J=8.6 Hz, 2H), 6.92 (s, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 2.00 (s, 6H); ESI MS m/z 393 [(M+H)+, calcd for C21H21N4O2S, 393.1].

Aufarbeitung

  1. customwas degassed with N2 for 10 min
  2. temperaturecooled to room temperature
  3. extractionextracted (3×) with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-069cf8aee69d4ce4b43db1ad2e107cda
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07112585B2

Notizen zur Reaktion

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