Sodium Carbonate → 3-(4-chlorobenzyl)-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-one

HRID 2241220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241220
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11](Br)=[CH:10][N:9]=[CH:8]2)=[CH:4][CH:3]=1.[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]=1[F:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Li+].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:26]([F:34])[CH:27]=3)=[CH:10][N:9]=[CH:8]2)=[CH:4][CH:3]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 663104043-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-one

Produkt 1

HCID 685138743-(4-chlorobenzyl)-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-oneAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a round bottom flask was added 3-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-one (0.388 g, 1.30 mmol), 4-benzyloxy-3-fluorophenylboronic acid (0.382 g, 1.55 mmol), Pd(PPh3)4 (0.0748 g, 0.0648 mmol), LiCl (0.275 g, 6.48 mmol), dioxane (10 mL) and 2 M aqueous sodium carbonate solution (5 mL). The reaction mixture was stirred at 10° C. for 1 hour, then quenched the reaction by pouring the mixture into water and diluting with ethyl acetate. The organic layer washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (Biotage 40S) to afford the title compound as white solid (0.17 g, 31.2% yield). LRMS (APCI pos) m/e 421.0 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.15 (s, 1H), 8.02 (s, 1H), 7.49-7.54 (m, 1H), 7.42-7.46 (m, 2H), 7.36-7.41 (m, 3H), 7.32-7.35 (m, 5H), 5.18 (s, 2H), 5.12 (s, 2H).

Aufarbeitung

  1. customquenched
  2. customthe reaction
  3. washThe organic layer washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (Biotage 40S)

Quellen und Nachweise

ORD-Eintrag
ord-dce872c9e1b347518f5b11202058ba8c
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

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