Hexane → HCID 46215810, Verbindung

HRID 2367176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367176
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.O.[NH2:26][NH2:27].CCOC(C)=O.CCCCCC>CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:27][N:26]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 58504409HCID 58504409, Verbindung

Produkt 1

HCID 46215810HCID 46215810, VerbindungAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 4-{2-amino-6-[(phenylmethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (367 mg, 1.15 mmol) in EtOH (10 mL) was added hydrazine monohydrate (1.0 mL, 20.4 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto water and EtOAc. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford crude product (280 mg). This material was dissolved in EtOH. Hexane was added until a precipitate began to form (a spatula was used to scratch the walls). The mixture was decanted and the solid was dried under vacuum to afford the title compound (150 mg, 39%) as a tan solid. LC-MS (ES) m/z=332 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 4.59 (s, 2H), 6.29 (s, 1H), 7.23 (m, 1H), 7.28-7.38 (m, 4H), 7.41 (d, J=8.3 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.75 (s, 1H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford crude product (280 mg)
  8. customto form (a spatula
  9. customThe mixture was decanted
  10. customthe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c1e7a20566dc488c841f9522fc5950d7
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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