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Triphenylphosphine → HCID 11385276, Verbindung

HRID 2216314
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216314
[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([Sn](CCCC)(CCCC)[C:40]1[CH:41]=[N:42][CH:43]=[N:44][CH:45]=1)CCC.[Li+].[Cl-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[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]3[CH:41]=[N:42][CH:43]=[N:44][CH:45]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 27632495-(Tributylstannyl)pyrimidineHCID 86595018HCID 86595018, Verbindung

Produkt 1

HCID 11385276HCID 11385276, Verbindung
Ausbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (95 mg, 0.18 mmol), prepared by the method described in Example 22, 5-tributylstannanyl-pyrimidine (75 mg, 0.20 mmol), LiCl (23 mg, 0.55 mmol) and DMF (4 mL) was deoxygenated with N2 for 10 min, and then Pd(PPh3)2Cl2 (13 mg, 0.018 mmol) and PPh3 (10 mg, 0.036 mmol) were added. The mixture was heated at 150° C. under N2 for 2 h and then cooled to room temperature. Saturated aqueous KF was added, and the mixture was extracted three times with CH2Cl2. 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 (50:50 hexanes/EtOAc) to provide the target compound (66 mg, 80%) as a white solid: mp 210–212° C.; 1H NMR (300 MHz, CDCl3) δ 9.29 (s, 1H), 8.96 (s, 1H), 8.80 (s, 1H), 8.30 (br s, 1H), 8.13 (d, J=8.5 Hz, 2H), 7.76 (d, J=8.5 Hz, 2H), 6.93 (s, 2H), 2.41 (s, 3H), 2.31 (s, 3H), 2.03 (s, 6H); APCI MS m/z 446 [(M+H)+, calcd for C24H24N5O2S, 446.2].

Aufarbeitung

  1. customprepared by the method
  2. customwas deoxygenated with N2 for 10 min
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted three times with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a25509b4bad04543981001713937ec75
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07112585B2

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