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Potassium Carbonate → HCID 57961668, Verbindung

HRID 541800
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 541800
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)=[O:6].[Cl:25][C:26]1[N:31]=[C:30](Cl)[C:29]([Cl:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([NH:7][C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[CH:11]=[CH:12][CH:13]=2)=[O:6])[C:29]([Cl:33])=[CH:28][N:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961539HCID 57961539, Verbindung

Produkt 1

HCID 57961668HCID 57961668, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {3-[(3-aminobenzoyl)amino]phenyl}carbamate (0.500 g, 1.53 mol) and 2,4,5-trichloropyrimidine (0.25 g, 1.4 mmol) in DMF (3.7 mL) was added potassium carbonate (0.29 g, 2.1 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated (sat'd) NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice and the combined organics were washed with water, dried, filtered and concentrated to give 800 mg of crude product, which was purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane) to give the desired product (66 mg, 10%). LCMS for C22H21Cl2N5O3 (M-tBu+H)+: m/z=420.0, 418.1. 1H NMR (400 MHz, CD3OD): δ 8.26 (s, 1H), 8.11 (t, J=2.0 Hz, 1H), 7.89 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 7.85 (t, J=2.0 Hz, 1H), 7.74 (ddd, J=7.6, 2.0, 0.8 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 7.19 (m, 1H), 1.52 (s, 9H).

Aufarbeitung

  1. customThe reaction was quenched with saturated (sat'd) NH4Cl and water
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washthe combined organics were washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give 800 mg of crude product, which
  10. customwas purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d63a842b8b4d45a683872040d8a05653
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871753B2

Notizen zur Reaktion

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