Dimethylformamide → HCID 86710192, Verbindung

HRID 2284430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284430
Br[C:2]1[CH:11]=[N:10][C:9]2[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:7][C:6]([Cl:18])=[N:5][C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>C1COCC1>[Cl:18][C:6]1[N:7]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[N:10]=[CH:11][C:2]([CH:26]=[O:27])=[CH:3][C:4]=2[N:5]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 86665768HCID 86665768, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 86710192HCID 86710192, VerbindungAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a 50 mL round bottom flask, 4-(7-bromo-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine (3.0 g, 0.0091 mol—Preparation 3) and dry THF (15 mL) were added under nitrogen atmosphere and then cooled to −78° C. To the reaction flask, 2.5 M n-butyl lithium (4.4 mL, 0.0109 mol) was slowly added and the reaction mixture was stirred at −78° C. for 30 minutes. To the reaction mixture, N,N-dimethylformamide (1.27 mL, 0.0164 mol) was added and the reaction mixture allowed to warm to 0° C. The reaction mass was quenched with 10% aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to provide the crude product. The crude product was purified by column chromatography (60-120 silica gel, 10-40% ethyl acetate) to provide the title compound as a light yellow solid (0.8 g, 31%). 1H NMR (300 MHz, CDCl3): δ 10.24 (s, 1H), 9.11 (d, J=2.1 Hz, 1H), 8.41 (d, J=2.1 Hz, 1H), 3.91 (t, J=4.8 Hz, 8H): LC-MS (ESI): Calculated mass. 278.06, Observed mass [M+H]+: 279.0 (RT=0.66 min).

Aufarbeitung

  1. temperatureto warm to 0° C
  2. customThe reaction mass was quenched with 10% aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto provide the crude product
  8. customThe crude product was purified by column chromatography (60-120 silica gel, 10-40% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-29429fe6c68642cdaae9119c6d219a80
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145411B2

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