Hydrogen Bromide → HCID 86267409, Verbindung

HRID 709988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709988
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([NH:29][CH3:30])[N:4]=1.Br>C(O)(=O)C>[CH3:28][C:11]1[N:10]=[C:9]([C:8]2[C:3](=[O:2])[NH:4][C:5]([NH:29][CH3:30])=[N:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[CH:17]=1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 90416670HCID 90416670, Verbindung

Produkt 1

HCID 86267409HCID 86267409, VerbindungAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 4-methoxy-N-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.10 g, 0.25 mmol) in acetic acid (5 mL) was treated with HBr (0.12 mL, 1.0 mmol) and heated at 90° C. for 4 h. The mixture was cooled to RT, quenched with ice water, treated with NaHCO3 and NaCl, and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness, the resulting material treated with MeCN (3 mL) and the solid was collected via filtration to afford 5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(methylamino)pyrimidin-4(3H)-one (52 mg, 53%). 1H NMR (400 MHz, DMSO-d6): δ 11.26 (s, 1H), 8.70 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.28 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.70 (br s, 1H), 6.61 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 2.85 (d, J=4.7 Hz, 3H), 2.35 (s, 3H); MS (ESI) m/z: 390.2 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. customquenched with ice water
  3. additiontreated with NaHCO3 and NaCl
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionthe resulting material treated with MeCN (3 mL)
  8. filtrationthe solid was collected via filtration

Quellen und Nachweise

ORD-Eintrag
ord-25ccce6cccbd4fe8aba6390b2a124e45
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181223B2

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