Triethylamine → HCID 22347523, Verbindung

HRID 897148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897148
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:3]1=2.[C:13](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:14].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:3]1=2

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 219345911,6-Dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Produkt 1

HCID 22347523HCID 22347523, VerbindungAusbeute 118,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1,6-dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (1.14 g, 7 mmol), di-tert-butyl dicarbonate (2.29 g, 10.5 mmol), DMAP (100 mg) and triethylamine (1.46 mL, 10.5 mmol) in 30 mL THF was refluxed 72 hours under N2. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate. The mixture was washed with brine, dried over Na2SO4. After filtration and concentration at reduced pressure, the crude mixture was purified by flash chromatography on silica gel (40% EA/Hex) to afford the desired product (1.6 g, 90% yield) as yellow oil. H NMR (400 MHz, CDCl3) δ 1.51 (s, 9H), 2.40 (s, 3H), 2.90 (s, 3H), 3.28 (t, 2H), 3.83 (m, 2H), 6.78 (d, 1H), 6.83(d, 2H). Step 6. Synthesis of tert-butyl 6-(2-ethoxy-2-oxoethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate.

Aufarbeitung

  1. washThe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration at reduced pressure
  4. customthe crude mixture was purified by flash chromatography on silica gel (40% EA/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-5eb9df62633047c9a11865c62c4e596a
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921767B2

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