Dimethylformamide → HCID 59852844, Verbindung

HRID 1670209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670209
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O.C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=3[F:18])[CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 59853046HCID 59853046, Verbindung

Produkt 1

HCID 59852844HCID 59852844, VerbindungAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-chloro-4-(2-fluoro-4-nitrophenoxy)pyrimidine (0.66 g, 2.44 mmol), 4-methoxybenzylamine (0.34 g, 3.45 mmol), K2CO3 (0.37 g, 2.66 mmol), and DMF (15 mL) was heated at 100° C. for 1 h. The mixture was cooled, diluted with H2O (100 mL) and extracted with EtOAc (100 mL). The organic phase was washed twice each with saturated NaHCO3 solution and brine. The organics were dried (MgSO4) and concentrated to give the crude product. Flash chromatography on SiO2 using 1-3% MeOH in CH2Cl2 as the eluent gave the title compound (275 mg, 29%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.40-8.21 (m, 2H), 8.16 (dd, 1H, J=8.8, 1.7 Hz), 7.98 (br s, 0.5H), 7.73-7.55 (m, 1.5H), 7.16 (br s, 1H), 6.85-6.71 (m, 3H), 6.37 (s, 1H), 4.43 (br s, 1H), 3.95 (br s, 1H), 3.69 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic phase was washed twice each with saturated NaHCO3 solution and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-1f1007ae54a94714b30f7ad6c20b779c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989477B2

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